Mosquito-Derived Anophelin Sulfoproteins Are Potent Antithrombotics - Watson, Emma E.; Liu, Xuyu; Thompson, Robert E.; Ripoll-Rozada, Jorge; Wu, Mike; Alwis, Imala; Gori, Alessandro; Loh, Choy-Theng; Parker, Benjamin L.; Otting, Gottfried; Jackson, Shaun; Pereira, Pedro José Barbosa; et al. (ACS Central Science, 2018)

Mosquito-Derived Anophelin Sulfoproteins Are Potent Antithrombotics - Watson, Emma E.; Liu, Xuyu; Thompson, Robert E.; Ripoll-Rozada, Jorge; Wu, Mike; Alwis, Imala; Gori, Alessandro; Loh, Choy-Theng; Parker, Benjamin L.; Otting, Gottfried; Jackson, Shaun; Pereira, Pedro José Barbosa; et al. (ACS Central Science, 2018)

Synthetic Glycoforms Reveal Carbohydrate-Dependent Bioactivity of Human Saposin D - Graf, Christopher G. F.; Schulz, Christian; Schmälzlein, Marina; Heinlein, Christian; Mönnich, Manuel; Perkams, Lukas; Püttner, Markus; Boos, Irene; Hessefort, Markus; Lombana Sanchez, Jose Nelson; Weyand, Michael; Steegborn, Clemens; et al. (Angewandte Chemie International Edition, 2017)

Synthetic Glycoforms Reveal Carbohydrate-Dependent Bioactivity of Human Saposin D - Graf, Christopher G. F.; Schulz, Christian; Schmälzlein, Marina; Heinlein, Christian; Mönnich, Manuel; Perkams, Lukas; Püttner, Markus; Boos, Irene; Hessefort, Markus; Lombana Sanchez, Jose Nelson; Weyand, Michael; Steegborn, Clemens; et al. (Angewandte Chemie International Edition, 2017)

Synthesis of the sphingolipid activator protein, saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element - Hojo, Hironobu; Katayama, Hidekazu; Tano, Chiharu; Nakahara, Yuko; Yoneshige, Azusa; Matsuda, Junko; Sohma, Youhei; Kiso, Yoshiaki; Nakahara, Yoshiaki (Tetrahedron Letters, 2011)

Synthesis of the sphingolipid activator protein, saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element - Hojo, Hironobu; Katayama, Hidekazu; Tano, Chiharu; Nakahara, Yuko; Yoneshige, Azusa; Matsuda, Junko; Sohma, Youhei; Kiso, Yoshiaki; Nakahara, Yoshiaki (Tetrahedron Letters, 2011)

A sensitive fluorescence monitor for the detection of activated Ras: total chemical synthesis of site-specifically labeled Ras binding domain of c-Raf1 immobilized on a surface - Becker, Christian F.W; Hunter, Christie L; Seidel, Ralf P; Kent, Stephen B.H; Goody, Roger S; Engelhard, Martin (Chemistry & Biology, 2001)

A sensitive fluorescence monitor for the detection of activated Ras: total chemical synthesis of site-specifically labeled Ras binding domain of c-Raf1 immobilized on a surface - Becker, Christian F.W; Hunter, Christie L; Seidel, Ralf P; Kent, Stephen B.H; Goody, Roger S; Engelhard, Martin (Chemistry & Biology, 2001)

Mirror Image Forms of Snow Flea Antifreeze Protein Prepared by Total Chemical Synthesis Have Identical Antifreeze Activities - Pentelute, Brad L.; Gates, Zachary P.; Dashnau, Jennifer L.; Vanderkooi, Jane M.; Kent, Stephen B. H. (Journal of the American Chemical Society, 2008)

Mirror Image Forms of Snow Flea Antifreeze Protein Prepared by Total Chemical Synthesis Have Identical Antifreeze Activities - Pentelute, Brad L.; Gates, Zachary P.; Dashnau, Jennifer L.; Vanderkooi, Jane M.; Kent, Stephen B. H. (Journal of the American Chemical Society, 2008)

Functional Characterization and NMR Spectroscopy on Full-Length Vpu from HIV-1 Prepared by Total Chemical Synthesis - Kochendoerfer, Gerd G.; Jones, David H.; Lee, Sangwon; Oblatt-Montal, Myrta; Opella, Stanley J.; Montal, Mauricio (Journal of the American Chemical Society, 2004)

A chemical approach for the synthesis of the DNA-binding domain of the oncoprotein MYC - Calo-Lapido, Renata; Penas, Cristina; Jiménez-Balsa, Adrián; Vázquez, M. Eugenio; Mascareñas, José L. (Organic & Biomolecular Chemistry, 2019)
We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). , We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). Both routes allowed the efficient synthesis of a miniprotein which is capable of heterodimerizing with MAX, and replicate the DNA binding of the native protein. The versatility of the reported synthetic approach enabled the straightforward preparation of MYC and Omomyc analogues, as well as fluorescently labeled derivatives.

Chemoenzymatic Synthesis of Hydrophobic Glycoprotein: Synthesis of Saposin C Carrying Complex-Type Carbohydrate - Hojo, Hironobu; Tanaka, Hiromasa; Hagiwara, Masashi; Asahina, Yuya; Ueki, Akiharu; Katayama, Hidekazu; Nakahara, Yuko; Yoneshige, Azusa; Matsuda, Junko; Ito, Yukishige; Nakahara, Yoshiaki (The Journal of Organic Chemistry, 2012)

Total chemical synthesis of dengue 2 virus capsid protein via native chemical ligation: Role of the conserved salt-bridge - Zhan, Changyou; Zhao, Le; Chen, Xishan; Lu, Wei-Yue; Lu, Wuyuan (Bioorganic & Medicinal Chemistry, 2013)

Functional Characterization and NMR Spectroscopy on Full-Length Vpu from HIV-1 Prepared by Total Chemical Synthesis - Kochendoerfer, Gerd G.; Jones, David H.; Lee, Sangwon; Oblatt-Montal, Myrta; Opella, Stanley J.; Montal, Mauricio (Journal of the American Chemical Society, 2004)

A chemical approach for the synthesis of the DNA-binding domain of the oncoprotein MYC - Calo-Lapido, Renata; Penas, Cristina; Jiménez-Balsa, Adrián; Vázquez, M. Eugenio; Mascareñas, José L. (Organic & Biomolecular Chemistry, 2019)
We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). , We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). Both routes allowed the efficient synthesis of a miniprotein which is capable of heterodimerizing with MAX, and replicate the DNA binding of the native protein. The versatility of the reported synthetic approach enabled the straightforward preparation of MYC and Omomyc analogues, as well as fluorescently labeled derivatives.

Chemoenzymatic Synthesis of Hydrophobic Glycoprotein: Synthesis of Saposin C Carrying Complex-Type Carbohydrate - Hojo, Hironobu; Tanaka, Hiromasa; Hagiwara, Masashi; Asahina, Yuya; Ueki, Akiharu; Katayama, Hidekazu; Nakahara, Yuko; Yoneshige, Azusa; Matsuda, Junko; Ito, Yukishige; Nakahara, Yoshiaki (The Journal of Organic Chemistry, 2012)

Total chemical synthesis of dengue 2 virus capsid protein via native chemical ligation: Role of the conserved salt-bridge - Zhan, Changyou; Zhao, Le; Chen, Xishan; Lu, Wei-Yue; Lu, Wuyuan (Bioorganic & Medicinal Chemistry, 2013)

Convergent synthesis of MUC1 glycopeptides via serine ligation - Xu, Ci; Lam, Hiu Yung; Zhang, Yinfeng; Li, Xuechen (Chemical Communications, 2013)

An explorative study towards the chemical synthesis of the immunoglobulin G1 Fc CH3 domain - Grassi, Luigi; Roschger, Cornelia; Stanojlović, Vesna; Cabrele, Chiara (Journal of Peptide Science, 2018)

Convergent synthesis of MUC1 glycopeptides via serine ligation - Xu, Ci; Lam, Hiu Yung; Zhang, Yinfeng; Li, Xuechen (Chemical Communications, 2013)

An explorative study towards the chemical synthesis of the immunoglobulin G1 Fc CH3 domain - Grassi, Luigi; Roschger, Cornelia; Stanojlović, Vesna; Cabrele, Chiara (Journal of Peptide Science, 2018)

Chimeric protein probes for C5a receptors through fusion of the anaphylatoxin C5a core region with a small-molecule antagonist - Zuo, Chao; Shi, Wei-Wei; Chen, Xiao-Xu; Glatz, Marie; Riedl, Bernd; Flamme, Ingo; Pook, Elisabeth; Wang, Jiawei; Fang, Ge-Min; Bierer, Donald; Liu, Lei (Science China Chemistry, 2019)

Efficient one-pot synthesis of CXCL14 and its derivative using an N -sulfanylethylanilide peptide as a peptide thioester equivalent and their biological evaluation - Tsuji, Kohei; Tanegashima, Kosuke; Sato, Kohei; Sakamoto, Ken; Shigenaga, Akira; Inokuma, Tsubasa; Hara, Takahiko; Otaka, Akira (Bioorganic & Medicinal Chemistry, 2015)

A tetrameric protein scaffold as a nano-carrier of antitumor peptides for cancer therapy - Ma, Bohan; Niu, Fan; Qu, Xiaoyan; He, Wangxiao; Feng, Chao; Wang, Simeng; Ouyang, Zhenlin; Yan, Jin; Wen, Yurong; Xu, Dan; Shao, Yongping; Ma, Peter X.; et al. (Biomaterials, 2019)

Chimeric protein probes for C5a receptors through fusion of the anaphylatoxin C5a core region with a small-molecule antagonist - Zuo, Chao; Shi, Wei-Wei; Chen, Xiao-Xu; Glatz, Marie; Riedl, Bernd; Flamme, Ingo; Pook, Elisabeth; Wang, Jiawei; Fang, Ge-Min; Bierer, Donald; Liu, Lei (Science China Chemistry, 2019)

Efficient one-pot synthesis of CXCL14 and its derivative using an N -sulfanylethylanilide peptide as a peptide thioester equivalent and their biological evaluation - Tsuji, Kohei; Tanegashima, Kosuke; Sato, Kohei; Sakamoto, Ken; Shigenaga, Akira; Inokuma, Tsubasa; Hara, Takahiko; Otaka, Akira (Bioorganic & Medicinal Chemistry, 2015)

A tetrameric protein scaffold as a nano-carrier of antitumor peptides for cancer therapy - Ma, Bohan; Niu, Fan; Qu, Xiaoyan; He, Wangxiao; Feng, Chao; Wang, Simeng; Ouyang, Zhenlin; Yan, Jin; Wen, Yurong; Xu, Dan; Shao, Yongping; Ma, Peter X.; et al. (Biomaterials, 2019)

Application of N–C- or C–N-directed sequential native chemical ligation to the preparation of CXCL14 analogs and their biological evaluation - Tsuji, Kohei; Shigenaga, Akira; Sumikawa, Yoshitake; Tanegashima, Kosuke; Sato, Kohei; Aihara, Keisuke; Hara, Takahiko; Otaka, Akira (Bioorganic & Medicinal Chemistry, 2011)

Chemical Synthesis and Structure of the Prokineticin Bv8 - Morales, Rodrigo A. V.; Daly, Norelle L.; Vetter, Irina; Mobli, Mehdi; Napier, Ian A.; Craik, David J.; Lewis, Richard J.; Christie, MacDonald J.; King, Glenn F.; Alewood, Paul F.; Durek, Thomas (ChemBioChem, 2010)

Application of N–C- or C–N-directed sequential native chemical ligation to the preparation of CXCL14 analogs and their biological evaluation - Tsuji, Kohei; Shigenaga, Akira; Sumikawa, Yoshitake; Tanegashima, Kosuke; Sato, Kohei; Aihara, Keisuke; Hara, Takahiko; Otaka, Akira (Bioorganic & Medicinal Chemistry, 2011)

Efficient chemical synthesis of human complement protein C3a - Ghassemian, Artin; Wang, Ching-I Anderson; Yau, Mei-Kwan; Reid, Robert C.; Lewis, Richard J.; Fairlie, David P.; Alewood, Paul F.; Durek, Thomas (Chemical Communications, 2013)

Chemical Synthesis and Structure of the Prokineticin Bv8 - Morales, Rodrigo A. V.; Daly, Norelle L.; Vetter, Irina; Mobli, Mehdi; Napier, Ian A.; Craik, David J.; Lewis, Richard J.; Christie, MacDonald J.; King, Glenn F.; Alewood, Paul F.; Durek, Thomas (ChemBioChem, 2010)

Efficient chemical synthesis of human complement protein C3a - Ghassemian, Artin; Wang, Ching-I Anderson; Yau, Mei-Kwan; Reid, Robert C.; Lewis, Richard J.; Fairlie, David P.; Alewood, Paul F.; Durek, Thomas (Chemical Communications, 2013)

Determinants of High-Affinity Binding and Receptor Activation in the N-Terminus of CCL-19 (MIP-3β) - Ott, T. R.; Lio, F. M.; Olshefski, D.; Liu, X.-J.; Struthers, R. S.; Ling, N. (Biochemistry, 2004)

Determinants of High-Affinity Binding and Receptor Activation in the N-Terminus of CCL-19 (MIP-3β) - Ott, T. R.; Lio, F. M.; Olshefski, D.; Liu, X.-J.; Struthers, R. S.; Ling, N. (Biochemistry, 2004)

Europium-Labeled Synthetic C3a Protein as a Novel Fluorescent Probe for Human Complement C3a Receptor - Dantas de Araujo, Aline; Wu, Chongyang; Wu, Kai-Chen; Reid, Robert C.; Durek, Thomas; Lim, Junxian; Fairlie, David P. (Bioconjugate Chemistry, 2017)

Europium-Labeled Synthetic C3a Protein as a Novel Fluorescent Probe for Human Complement C3a Receptor - Dantas de Araujo, Aline; Wu, Chongyang; Wu, Kai-Chen; Reid, Robert C.; Durek, Thomas; Lim, Junxian; Fairlie, David P. (Bioconjugate Chemistry, 2017)

Resin-Bound Crypto-Thioester for Native Chemical Ligation - Naruse, Naoto; Ohkawachi, Kento; Inokuma, Tsubasa; Shigenaga, Akira; Otaka, Akira (Organic Letters, 2018)

Resin-Bound Crypto-Thioester for Native Chemical Ligation - Naruse, Naoto; Ohkawachi, Kento; Inokuma, Tsubasa; Shigenaga, Akira; Otaka, Akira (Organic Letters, 2018)

Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation - Naruse, Naoto; Kobayashi, Daishiro; Ohkawachi, Kento; Shigenaga, Akira; Otaka, Akira (The Journal of Organic Chemistry, 2020)

Copper-Mediated Deprotection of Thiazolidine and Selenazolidine Derivatives Applied to Native Chemical Ligation - Naruse, Naoto; Kobayashi, Daishiro; Ohkawachi, Kento; Shigenaga, Akira; Otaka, Akira (The Journal of Organic Chemistry, 2020)

Chemical Syntheses and Biological Evaluation of CXCL14 and Its Site-Selectively Modified Methionine Sulfoxide-Containing Derivatives - Cai, Zonghui; Wei, Qijia; Li, Xiujuan; Luan, Yi; Dong, Suwei (The Journal of Organic Chemistry, 2020)

Chemical Syntheses and Biological Evaluation of CXCL14 and Its Site-Selectively Modified Methionine Sulfoxide-Containing Derivatives - Cai, Zonghui; Wei, Qijia; Li, Xiujuan; Luan, Yi; Dong, Suwei (The Journal of Organic Chemistry, 2020)

Synthesis by native chemical ligation and crystal structure of human CCL2 - Grygiel, Tami L. R.; Teplyakov, Alexey; Obmolova, Galina; Stowell, Nicole; Holland, Reannon; Nemeth, Jennifer F.; Pomerantz, Steven C.; Kruszynski, Marian; Gilliland, Gary L. (Biopolymers, 2010)

Synthesis by native chemical ligation and crystal structure of human CCL2 - Grygiel, Tami L. R.; Teplyakov, Alexey; Obmolova, Galina; Stowell, Nicole; Holland, Reannon; Nemeth, Jennifer F.; Pomerantz, Steven C.; Kruszynski, Marian; Gilliland, Gary L. (Biopolymers, 2010)

N-to-C Sequential Ligation Using Peptidyl N,N -Bis(2-mercaptoethyl)amide Building Blocks - Yang, Renliang; Hou, Wen; Zhang, Xiaohong; Liu, Chuan-Fa (Organic Letters, 2012)

N-to-C Sequential Ligation Using Peptidyl N,N -Bis(2-mercaptoethyl)amide Building Blocks - Yang, Renliang; Hou, Wen; Zhang, Xiaohong; Liu, Chuan-Fa (Organic Letters, 2012)

The Chemical Synthesis of the Collagenous Domain of the Hormone Adiponectin - Harris, Paul W. R.; Brimble, Margaret A. (International Journal of Peptide Research and Therapeutics, 2012)

The Chemical Synthesis of the Collagenous Domain of the Hormone Adiponectin - Harris, Paul W. R.; Brimble, Margaret A. (International Journal of Peptide Research and Therapeutics, 2012)

A Versatile Strategy for the Semisynthetic Production of Ser65 Phosphorylated Ubiquitin and Its Biochemical and Structural Characterisation - Han, Cong; Pao, Kuan-Chuan; Kazlauskaite, Agne; Muqit, Miratul M. K.; Virdee, Satpal (ChemBioChem, 2015)

A Versatile Strategy for the Semisynthetic Production of Ser65 Phosphorylated Ubiquitin and Its Biochemical and Structural Characterisation - Han, Cong; Pao, Kuan-Chuan; Kazlauskaite, Agne; Muqit, Miratul M. K.; Virdee, Satpal (ChemBioChem, 2015)

Chemical Synthesis of a Glycoprotein Having an Intact Human Complex-Type Sialyloligosaccharide under the Boc and Fmoc Synthetic Strategies - Yamamoto, Naoki; Tanabe, Yasutaka; Okamoto, Ryo; Dawson, Philip E.; Kajihara, Yasuhiro (Journal of the American Chemical Society, 2008)

Chemical Synthesis of a Glycoprotein Having an Intact Human Complex-Type Sialyloligosaccharide under the Boc and Fmoc Synthetic Strategies - Yamamoto, Naoki; Tanabe, Yasutaka; Okamoto, Ryo; Dawson, Philip E.; Kajihara, Yasuhiro (Journal of the American Chemical Society, 2008)

Total Chemical Synthesis and X-ray Crystal Structure of a Protein Diastereomer: [D-Gln 35]Ubiquitin - Bang, Duhee; Makhatadze, George I.; Tereshko, Valentina; Kossiakoff, Anthony A.; Kent, Stephen B. (Angewandte Chemie International Edition, 2005)

Total Chemical Synthesis and X-ray Crystal Structure of a Protein Diastereomer: [D-Gln 35]Ubiquitin - Bang, Duhee; Makhatadze, George I.; Tereshko, Valentina; Kossiakoff, Anthony A.; Kent, Stephen B. (Angewandte Chemie International Edition, 2005)

Chemical synthesis of Ub-AMC via ligation of peptide hydrazides - Liang, Jun; Fang, GeMin; Huang, XiuLiang; Mei, ZiQing; Li, Juan; Tian, ChangLin; Liu, Lei (Science China Chemistry, 2013)

Chemical synthesis of Ub-AMC via ligation of peptide hydrazides - Liang, Jun; Fang, GeMin; Huang, XiuLiang; Mei, ZiQing; Li, Juan; Tian, ChangLin; Liu, Lei (Science China Chemistry, 2013)

Synthesis of l - and d -Ubiquitin by One-Pot Ligation and Metal-Free Desulfurization - Huang, Yi-Chao; Chen, Chen-Chen; Gao, Shuai; Wang, Ye-Hai; Xiao, Hua; Wang, Feng; Tian, Chang-Lin; Li, Yi-Ming (Chemistry - A European Journal, 2016)

Synthesis of l - and d -Ubiquitin by One-Pot Ligation and Metal-Free Desulfurization - Huang, Yi-Chao; Chen, Chen-Chen; Gao, Shuai; Wang, Ye-Hai; Xiao, Hua; Wang, Feng; Tian, Chang-Lin; Li, Yi-Ming (Chemistry - A European Journal, 2016)

Chemical Synthesis of Glycoproteins with the Specific Installation of Gradient-Enriched 15 N-Labeled Amino Acids for Getting Insights into Glycoprotein Behavior - Minh Hien, Nguyen; Izumi, Masayuki; Sato, Hajime; Okamoto, Ryo; Kajihara, Yasuhiro (Chemistry - A European Journal, 2017)

Chemical Synthesis of Glycoproteins with the Specific Installation of Gradient-Enriched 15 N-Labeled Amino Acids for Getting Insights into Glycoprotein Behavior - Minh Hien, Nguyen; Izumi, Masayuki; Sato, Hajime; Okamoto, Ryo; Kajihara, Yasuhiro (Chemistry - A European Journal, 2017)

Ubiquitin 7-amino-4-carbamoylmethylcoumarin as an improved fluorogenic substrate for deubiquitinating enzymes - Li, Yi-Tong; Huang, Yi-Chao; Xu, Yang; Pan, Man; Li, Yi-Ming (Tetrahedron, 2016)

Ubiquitin 7-amino-4-carbamoylmethylcoumarin as an improved fluorogenic substrate for deubiquitinating enzymes - Li, Yi-Tong; Huang, Yi-Chao; Xu, Yang; Pan, Man; Li, Yi-Ming (Tetrahedron, 2016)

Acceleration of amyloid fibril formation by carboxyl-terminal truncation of human serum amyloid A - Tanaka, Masafumi; Kawakami, Toru; Okino, Nozomi; Sasaki, Kaoru; Nakanishi, Kiwako; Takase, Hiroka; Yamada, Toshiyuki; Mukai, Takahiro (Archives of Biochemistry and Biophysics, 2018)

Acceleration of amyloid fibril formation by carboxyl-terminal truncation of human serum amyloid A - Tanaka, Masafumi; Kawakami, Toru; Okino, Nozomi; Sasaki, Kaoru; Nakanishi, Kiwako; Takase, Hiroka; Yamada, Toshiyuki; Mukai, Takahiro (Archives of Biochemistry and Biophysics, 2018)

Exploring the Functional Consequences of Protein Backbone Alteration in Ubiquitin through Native Chemical Ligation - Werner, Halina M.; Estabrooks, Samuel K.; Preston, G. Michael; Brodsky, Jeffrey L.; Horne, W. Seth (ChemBioChem, 2019)

Exploring the Functional Consequences of Protein Backbone Alteration in Ubiquitin through Native Chemical Ligation - Werner, Halina M.; Estabrooks, Samuel K.; Preston, G. Michael; Brodsky, Jeffrey L.; Horne, W. Seth (ChemBioChem, 2019)

Efficient chemical synthesis for the analogue of ubiquitin-based probe Ub–AMC with native bioactivity - Xu, Ling; Xu, Yang; Qu, Qian; Guan, Chao-Jian; Chu, Guo-Chao; Shi, Jing; Li, Yi-Ming (RSC Advances, 2016)
The analogue of ubiquitin-based probe ubiquitin–7-amido-4-methylcoumarin (Ub–AMC) was efficiently synthesized through a methyl thioglycolate (MTG) assisted one-pot ligation–desulfurization protocol. , The analogue of ubiquitin-based probe ubiquitin–7-amido-4-methylcoumarin (Ub–AMC) was efficiently synthesized through a methyl thioglycolate (MTG) assisted one-pot ligation–desulfurization protocol. To obtain peptide segments with higher yield, norleucine (Nle) was used instead of methionine in the chemical synthesis procedure. Compared with native Ub–AMC, the analogue exhibits well-folded secondary structure and desired bioactivity for studying the DUB enzyme.

Efficient chemical synthesis for the analogue of ubiquitin-based probe Ub–AMC with native bioactivity - Xu, Ling; Xu, Yang; Qu, Qian; Guan, Chao-Jian; Chu, Guo-Chao; Shi, Jing; Li, Yi-Ming (RSC Advances, 2016)
The analogue of ubiquitin-based probe ubiquitin–7-amido-4-methylcoumarin (Ub–AMC) was efficiently synthesized through a methyl thioglycolate (MTG) assisted one-pot ligation–desulfurization protocol. , The analogue of ubiquitin-based probe ubiquitin–7-amido-4-methylcoumarin (Ub–AMC) was efficiently synthesized through a methyl thioglycolate (MTG) assisted one-pot ligation–desulfurization protocol. To obtain peptide segments with higher yield, norleucine (Nle) was used instead of methionine in the chemical synthesis procedure. Compared with native Ub–AMC, the analogue exhibits well-folded secondary structure and desired bioactivity for studying the DUB enzyme.

Chemical synthesis and racemic crystallization of rat C5a-desArg - Zuo, Chao; Zhang, Baochang; Wu, Meng; Bierer, Donald; Shi, Jing; Fang, Ge-Min (Chinese Chemical Letters, 2020)

Chemical synthesis and racemic crystallization of rat C5a-desArg - Zuo, Chao; Zhang, Baochang; Wu, Meng; Bierer, Donald; Shi, Jing; Fang, Ge-Min (Chinese Chemical Letters, 2020)

Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups - Neumann, Kevin; Farnung, Jakob; Baldauf, Simon; Bode, Jeffrey W. (Nature Communications, 2020)

Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups - Neumann, Kevin; Farnung, Jakob; Baldauf, Simon; Bode, Jeffrey W. (Nature Communications, 2020)

Invariant Gly Residue Is Important for α-Defensin Folding, Dimerization, and Function: A CASE STUDY OF THE HUMAN NEUTROPHIL α-DEFENSIN HNP1 - Zhao, Le; Ericksen, Bryan; Wu, Xueji; Zhan, Changyou; Yuan, Weirong; Li, Xu; Pazgier, Marzena; Lu, Wuyuan (Journal of Biological Chemistry, 2012)

Invariant Gly Residue Is Important for α-Defensin Folding, Dimerization, and Function: A CASE STUDY OF THE HUMAN NEUTROPHIL α-DEFENSIN HNP1 - Zhao, Le; Ericksen, Bryan; Wu, Xueji; Zhan, Changyou; Yuan, Weirong; Li, Xu; Pazgier, Marzena; Lu, Wuyuan (Journal of Biological Chemistry, 2012)

The Molt-Inhibiting Hormone in the American Crayfish Procambarus clarkii: Its Chemical Synthesis and Biological Activity - Sonobe, Haruyuki; Nishimura, Takayuki; Sonobe, Maki; Nakatsuji, Teruaki; Yanagihara, Ryoji; Kawakami, Toru; Aimoto, Saburo (General and Comparative Endocrinology, 2001)

The Molt-Inhibiting Hormone in the American Crayfish Procambarus clarkii: Its Chemical Synthesis and Biological Activity - Sonobe, Haruyuki; Nishimura, Takayuki; Sonobe, Maki; Nakatsuji, Teruaki; Yanagihara, Ryoji; Kawakami, Toru; Aimoto, Saburo (General and Comparative Endocrinology, 2001)

A New Method for Synthesis of Peptide Thioesters via Irreversible N-to-S Acyl Transfer - Zheng, Ji-Shen; Chen, Xin; Tang, Shan; Chang, Hao-Nan; Wang, Feng-Liang; Zuo, Chao (Organic Letters, 2014)

A New Method for Synthesis of Peptide Thioesters via Irreversible N-to-S Acyl Transfer - Zheng, Ji-Shen; Chen, Xin; Tang, Shan; Chang, Hao-Nan; Wang, Feng-Liang; Zuo, Chao (Organic Letters, 2014)

Total Chemical Synthesis and Biological Activities of Glycosylated and Non-Glycosylated Forms of the Chemokines CCL1 and Ser-CCL1 - Okamoto, Ryo; Mandal, Kalyaneswar; Ling, Morris; Luster, Andrew D.; Kajihara, Yasuhiro; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2014)

Total Chemical Synthesis and Biological Activities of Glycosylated and Non-Glycosylated Forms of the Chemokines CCL1 and Ser-CCL1 - Okamoto, Ryo; Mandal, Kalyaneswar; Ling, Morris; Luster, Andrew D.; Kajihara, Yasuhiro; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2014)

Photoprotected Peptide α -Ketoacids and Hydroxylamines for Iterative and One-Pot KAHA Ligations: Synthesis of NEDD8 - Thuaud, Frédéric; Rohrbacher, Florian; Zwicky, André; Bode, Jeffrey W. (Helvetica Chimica Acta, 2016)

Photoprotected Peptide α -Ketoacids and Hydroxylamines for Iterative and One-Pot KAHA Ligations: Synthesis of NEDD8 - Thuaud, Frédéric; Rohrbacher, Florian; Zwicky, André; Bode, Jeffrey W. (Helvetica Chimica Acta, 2016)

Total synthesis of snake toxin α-bungarotoxin and its analogues by hydrazide-based native chemical ligation - Guo, Xiao-Qi; Liang, Jun; Li, Ying; Zhang, Yong; Huang, Dongliang; Tian, Changlin (Chinese Chemical Letters, 2018)

Total synthesis of snake toxin α-bungarotoxin and its analogues by hydrazide-based native chemical ligation - Guo, Xiao-Qi; Liang, Jun; Li, Ying; Zhang, Yong; Huang, Dongliang; Tian, Changlin (Chinese Chemical Letters, 2018)

Efficient Palladium-Assisted One-Pot Deprotection of (Acetamidomethyl)Cysteine Following Native Chemical Ligation and/or Desulfurization To Expedite Chemical Protein Synthesis - Maity, Suman Kumar; Jbara, Muhammad; Laps, Shay; Brik, Ashraf (Angewandte Chemie International Edition, 2016)

Efficient Palladium-Assisted One-Pot Deprotection of (Acetamidomethyl)Cysteine Following Native Chemical Ligation and/or Desulfurization To Expedite Chemical Protein Synthesis - Maity, Suman Kumar; Jbara, Muhammad; Laps, Shay; Brik, Ashraf (Angewandte Chemie International Edition, 2016)

Chemical synthesis of La1 isolated from the venom of the scorpion Liocheles australasiae and determination of its disulfide bonding pattern: Synthesis of La1 and Determination of Its Disulfide Bonding Pattern - Nagao, Junya; Miyashita, Masahiro; Nakagawa, Yoshiaki; Miyagawa, Hisashi (Journal of Peptide Science, 2015)

Chemical synthesis of La1 isolated from the venom of the scorpion Liocheles australasiae and determination of its disulfide bonding pattern: Synthesis of La1 and Determination of Its Disulfide Bonding Pattern - Nagao, Junya; Miyashita, Masahiro; Nakagawa, Yoshiaki; Miyagawa, Hisashi (Journal of Peptide Science, 2015)

Leveraging the Knorr Pyrazole Synthesis for the Facile Generation of Thioester Surrogates for use in Native Chemical Ligation - Flood, Dillon T.; Hintzen, Jordi C. J.; Bird, Michael J.; Cistrone, Philip A.; Chen, Jason S.; Dawson, Philip E. (Angewandte Chemie International Edition, 2018)

Leveraging the Knorr Pyrazole Synthesis for the Facile Generation of Thioester Surrogates for use in Native Chemical Ligation - Flood, Dillon T.; Hintzen, Jordi C. J.; Bird, Michael J.; Cistrone, Philip A.; Chen, Jason S.; Dawson, Philip E. (Angewandte Chemie International Edition, 2018)

Synthesis of proteins by native chemical ligation - Dawson, P.; Muir, T.; Clark-Lewis, I; Kent, S. (Science, 1994)

Synthesis of proteins by native chemical ligation - Dawson, P.; Muir, T.; Clark-Lewis, I; Kent, S. (Science, 1994)

Total chemical synthesis of the B1 domain of protein L from Peptostreptococcus magnus - Yang, Xiaoye; Fitzgerald, Michael C. (Bioorganic Chemistry, 2006)

Total chemical synthesis of the B1 domain of protein L from Peptostreptococcus magnus - Yang, Xiaoye; Fitzgerald, Michael C. (Bioorganic Chemistry, 2006)

Insitu thioester formation for protein ligation using α-methylcysteine - Burlina, Fabienne; Papageorgiou, George; Morris, Caroline; White, Peter D.; Offer, John (Chem. Sci., 2014)

Insitu thioester formation for protein ligation using α-methylcysteine - Burlina, Fabienne; Papageorgiou, George; Morris, Caroline; White, Peter D.; Offer, John (Chem. Sci., 2014)

Peptide Ligation at High Dilution via Reductive Diselenide-Selenoester Ligation - Chisholm, Timothy S.; Kulkarni, Sameer S.; Hossain, Khondker R.; Cornelius, Flemming; Clarke, Ronald J.; Payne, Richard J. (Journal of the American Chemical Society, 2020)

Peptide Ligation at High Dilution via Reductive Diselenide-Selenoester Ligation - Chisholm, Timothy S.; Kulkarni, Sameer S.; Hossain, Khondker R.; Cornelius, Flemming; Clarke, Ronald J.; Payne, Richard J. (Journal of the American Chemical Society, 2020)

Protein Synthesis by Solid-Phase Chemical Ligation Using a Safety Catch Linker - Brik, Ashraf; Keinan, Ehud; Dawson, Philip E. (The Journal of Organic Chemistry, 2000)

Protein Synthesis by Solid-Phase Chemical Ligation Using a Safety Catch Linker - Brik, Ashraf; Keinan, Ehud; Dawson, Philip E. (The Journal of Organic Chemistry, 2000)

Divergent Protein Synthesis of Bowman–Birk Protease Inhibitors, their Hydrodynamic Behavior and Co-crystallization with α-Chymotrypsin - Tornøe, Christian; Johansson, Eva; Wahlund, Per-Olof (Synlett, 2017)
A divergent protein synthesis strategy was executed to effectively synthesize Bowman–Birk protease inhibitor (BBI) analogues using native chemical ligation of peptide hydrazides. Grafting selected residues from a potent trypsin inhibitor, sunflower trypsin inhibitor-1, onto the α-chymotrypsin-binding loop of BBI, resulted in a fourfold improvement of α-chymotrypsin inhibition. The crystal structure of a synthetic BBI analogue co-crystallized with α-chymotrypsin confirmed the correct protein fold and showed a similar overall structure to unmodified BBI in complex with α-chymotrypsin. Dynamic light scattering showed that C-terminal truncation of BBI led to increased self-association.

Divergent Protein Synthesis of Bowman–Birk Protease Inhibitors, their Hydrodynamic Behavior and Co-crystallization with α-Chymotrypsin - Tornøe, Christian; Johansson, Eva; Wahlund, Per-Olof (Synlett, 2017)
A divergent protein synthesis strategy was executed to effectively synthesize Bowman–Birk protease inhibitor (BBI) analogues using native chemical ligation of peptide hydrazides. Grafting selected residues from a potent trypsin inhibitor, sunflower trypsin inhibitor-1, onto the α-chymotrypsin-binding loop of BBI, resulted in a fourfold improvement of α-chymotrypsin inhibition. The crystal structure of a synthetic BBI analogue co-crystallized with α-chymotrypsin confirmed the correct protein fold and showed a similar overall structure to unmodified BBI in complex with α-chymotrypsin. Dynamic light scattering showed that C-terminal truncation of BBI led to increased self-association.

Ag(I)-Catalyzed Cycloisomerization and Cyclization of Ketene Aminals: Construction of Azepine and 1,2-Dihydropyridine Derivatives - Nayak, Sanatan; Prabagar, B.; Ghosh, Nayan; Mallick, Rajendra; Sahoo, Akhila (Synthesis, 2017)
Silver-catalyzed cyclization and cycloisomerization of ketene N,N-acetals at room temperature has been developed to access a variety of highly substituted cyclobutene-fused azepine and 1,2-dihydropyridine derivatives. This cost-effective method is reliably implemented for the gram-scale synthesis of azepine and dihydropyridine derivatives. The iodo group in the periphery of the dihydropyridine motif can be functionalized with both Suzuki and Sonogashira reactions.

Ag(I)-Catalyzed Cycloisomerization and Cyclization of Ketene Aminals: Construction of Azepine and 1,2-Dihydropyridine Derivatives - Nayak, Sanatan; Prabagar, B.; Ghosh, Nayan; Mallick, Rajendra; Sahoo, Akhila (Synthesis, 2017)
Silver-catalyzed cyclization and cycloisomerization of ketene N,N-acetals at room temperature has been developed to access a variety of highly substituted cyclobutene-fused azepine and 1,2-dihydropyridine derivatives. This cost-effective method is reliably implemented for the gram-scale synthesis of azepine and dihydropyridine derivatives. The iodo group in the periphery of the dihydropyridine motif can be functionalized with both Suzuki and Sonogashira reactions.

Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability - Chen, Yi-Hung; Ellwart, Mario; Malakhov, Vladimir; Knochel, Paul (Synthesis, 2017)
Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture. 1 Introduction 2 Preparation of Organozinc Pivalates 2.1 Using Organic Halides as Substrates 2.2 Using a Directed Metalation on Functionalized Arenes and Heteroarenes 2.3 Preparation of Solid Allylic Zinc Pivalates 3 General Reactivity Patterns of Organozinc Pivalates 3.1 General Aspects 3.2 Transition-Metal-Catalyzed Cross-Couplings 3.3 Other Carbon–Carbon Bond-Forming Reactions Using Organozinc Pivalates 3.4 Preparation and Reactions of Solid, Salt-Stabilized Zinc Amide Enolates as New, Convenient Reformatsky Reagents 4 Conclusion

Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine - Malins, Lara R.; Mitchell, Nicholas J.; McGowan, Sheena; Payne, Richard J. (Angewandte Chemie International Edition, 2015)

Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability - Chen, Yi-Hung; Ellwart, Mario; Malakhov, Vladimir; Knochel, Paul (Synthesis, 2017)
Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture. 1 Introduction 2 Preparation of Organozinc Pivalates 2.1 Using Organic Halides as Substrates 2.2 Using a Directed Metalation on Functionalized Arenes and Heteroarenes 2.3 Preparation of Solid Allylic Zinc Pivalates 3 General Reactivity Patterns of Organozinc Pivalates 3.1 General Aspects 3.2 Transition-Metal-Catalyzed Cross-Couplings 3.3 Other Carbon–Carbon Bond-Forming Reactions Using Organozinc Pivalates 3.4 Preparation and Reactions of Solid, Salt-Stabilized Zinc Amide Enolates as New, Convenient Reformatsky Reagents 4 Conclusion

Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine - Malins, Lara R.; Mitchell, Nicholas J.; McGowan, Sheena; Payne, Richard J. (Angewandte Chemie International Edition, 2015)

Tandem Ligation of Unprotected Peptides through Thiaprolyl and Cysteinyl Bonds in Water † - Tam, James P.; Yu, Qitao; Yang, Jin-Long (Journal of the American Chemical Society, 2001)

Tandem Ligation of Unprotected Peptides through Thiaprolyl and Cysteinyl Bonds in Water † - Tam, James P.; Yu, Qitao; Yang, Jin-Long (Journal of the American Chemical Society, 2001)

Total chemical synthesis and biophysical characterization of the minimal isoform of the KChIP2 potassium channel regulatory subunit - Rajagopal, Sudarshan; Kent, Stephen B.H. (Protein Science, 2007)

Total chemical synthesis and biophysical characterization of the minimal isoform of the KChIP2 potassium channel regulatory subunit - Rajagopal, Sudarshan; Kent, Stephen B.H. (Protein Science, 2007)

Comparative Properties of Insulin-like Growth Factor 1 (IGF-1) and [Gly7D-Ala]IGF-1 Prepared by Total Chemical Synthesis - Sohma, Youhei; Pentelute, Brad L.; Whittaker, Jonathan; Hua, Qin-xin; Whittaker, Linda J.; Weiss, Michael A.; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2008)

Comparative Properties of Insulin-like Growth Factor 1 (IGF-1) and [Gly7D-Ala]IGF-1 Prepared by Total Chemical Synthesis - Sohma, Youhei; Pentelute, Brad L.; Whittaker, Jonathan; Hua, Qin-xin; Whittaker, Linda J.; Weiss, Michael A.; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2008)

Trifluoroethanethiol: An Additive for Efficient One-Pot Peptide Ligation−Desulfurization Chemistry - Thompson, Robert E.; Liu, Xuyu; Alonso-García, Noelia; Pereira, Pedro José Barbosa; Jolliffe, Katrina A.; Payne, Richard J. (Journal of the American Chemical Society, 2014)

Trifluoroethanethiol: An Additive for Efficient One-Pot Peptide Ligation−Desulfurization Chemistry - Thompson, Robert E.; Liu, Xuyu; Alonso-García, Noelia; Pereira, Pedro José Barbosa; Jolliffe, Katrina A.; Payne, Richard J. (Journal of the American Chemical Society, 2014)

Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid–hydroxylamine (KAHA) ligation - Rohrbacher, Florian; Zwicky, André; Bode, Jeffrey W. (Chemical Science, 2017)
The development of ligation conditions suitable for highly hydrophobic peptide segments allowed the first chemical synthesis of the head-to-tail cyclized protein AS-48. , An antibacterial cyclic AS-48 protein was chemically synthesized by α-ketoacid–hydroxylamine (KAHA) ligation. Initial challenges associated with the exceptionally hydrophobic segments arising from the amphiphilic nature of the protein were resolved by the development of bespoke reaction conditions for hydrophobic segments, using hexafluoroisopropanol (HFIP) as a co-solvent. The synthetic protein displays similar biological activity and properties to those of the native protein. To support the current understanding of its antibacterial mode of action, we demonstrate the ability of AS-48 to be incorporated into synthetic multilamellar vesicles (MLVs).

Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid–hydroxylamine (KAHA) ligation - Rohrbacher, Florian; Zwicky, André; Bode, Jeffrey W. (Chemical Science, 2017)
The development of ligation conditions suitable for highly hydrophobic peptide segments allowed the first chemical synthesis of the head-to-tail cyclized protein AS-48. , An antibacterial cyclic AS-48 protein was chemically synthesized by α-ketoacid–hydroxylamine (KAHA) ligation. Initial challenges associated with the exceptionally hydrophobic segments arising from the amphiphilic nature of the protein were resolved by the development of bespoke reaction conditions for hydrophobic segments, using hexafluoroisopropanol (HFIP) as a co-solvent. The synthetic protein displays similar biological activity and properties to those of the native protein. To support the current understanding of its antibacterial mode of action, we demonstrate the ability of AS-48 to be incorporated into synthetic multilamellar vesicles (MLVs).

Solvent-switchable continuous-breathing behaviour in a diamondoid metal–organic framework and its influence on CO2 versus CH4 selectivity - Carrington, Elliot J.; McAnally, Craig A.; Fletcher, Ashleigh J.; Thompson, Stephen P.; Warren, Mark; Brammer, Lee (Nature Chemistry, 2017)

Solvent-switchable continuous-breathing behaviour in a diamondoid metal–organic framework and its influence on CO2 versus CH4 selectivity - Carrington, Elliot J.; McAnally, Craig A.; Fletcher, Ashleigh J.; Thompson, Stephen P.; Warren, Mark; Brammer, Lee (Nature Chemistry, 2017)

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals - Silvi, Mattia; Verrier, Charlie; Rey, Yannick P.; Buzzetti, Luca; Melchiorre, Paolo (Nature Chemistry, 2017)

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals - Silvi, Mattia; Verrier, Charlie; Rey, Yannick P.; Buzzetti, Luca; Melchiorre, Paolo (Nature Chemistry, 2017)

A polymer nanoparticle with engineered affinity for a vascular endothelial growth factor (VEGF165) - Koide, Hiroyuki; Yoshimatsu, Keiichi; Hoshino, Yu; Lee, Shih-Hui; Okajima, Ai; Ariizumi, Saki; Narita, Yudai; Yonamine, Yusuke; Weisman, Adam C.; Nishimura, Yuri; Oku, Naoto; Miura, Yoshiko; et al. (Nature Chemistry, 2017)

A polymer nanoparticle with engineered affinity for a vascular endothelial growth factor (VEGF165) - Koide, Hiroyuki; Yoshimatsu, Keiichi; Hoshino, Yu; Lee, Shih-Hui; Okajima, Ai; Ariizumi, Saki; Narita, Yudai; Yonamine, Yusuke; Weisman, Adam C.; Nishimura, Yuri; Oku, Naoto; Miura, Yoshiko; et al. (Nature Chemistry, 2017)

Peptide self-cleavage at a canaline residue: application to a solubilizing tag system for native chemical ligation - Tsuda, Shugo; Nishio, Hideki; Yoshiya, Taku (Chemical Communications, 2018)
Taking advantage of the pH-dependent cleavage properties of canaline (Can), a novel solubilizing tag system for native chemical ligation using (Lys/Arg) n -Can was developed. , Canaline (Can) is a non-proteinogenic amino acid containing an aminooxy group in its side chain. Can-containing peptides can be synthesized by standard Fmoc SPPS using Fmoc-Can(2-Cl-Trt). Here, for the first time, a Can residue within a peptide sequence was found to spontaneously cleave the main chain amide bond under slightly acidic conditions (pH 4–5). Contrastingly, Can-containing peptides are completely stable under the acidic conditions for HPLC purification (pH ca. 2) and under the neutral conditions for native chemical ligation (NCL). Taking advantage of these unique pH-dependent properties of Can, a novel solubilizing tag system for NCL-mediated protein synthesis using (Lys/Arg) n -Can was developed.

Peptide self-cleavage at a canaline residue: application to a solubilizing tag system for native chemical ligation - Tsuda, Shugo; Nishio, Hideki; Yoshiya, Taku (Chemical Communications, 2018)
Taking advantage of the pH-dependent cleavage properties of canaline (Can), a novel solubilizing tag system for native chemical ligation using (Lys/Arg) n -Can was developed. , Canaline (Can) is a non-proteinogenic amino acid containing an aminooxy group in its side chain. Can-containing peptides can be synthesized by standard Fmoc SPPS using Fmoc-Can(2-Cl-Trt). Here, for the first time, a Can residue within a peptide sequence was found to spontaneously cleave the main chain amide bond under slightly acidic conditions (pH 4–5). Contrastingly, Can-containing peptides are completely stable under the acidic conditions for HPLC purification (pH ca. 2) and under the neutral conditions for native chemical ligation (NCL). Taking advantage of these unique pH-dependent properties of Can, a novel solubilizing tag system for NCL-mediated protein synthesis using (Lys/Arg) n -Can was developed.

Peptide αthioester formation using standard Fmoc-chemistry - von Eggelkraut-Gottanka, Regula; Klose, Annerose; Beck-Sickinger, Annette G.; Beyermann, Michael (Tetrahedron Letters, 2003)

Peptide αthioester formation using standard Fmoc-chemistry - von Eggelkraut-Gottanka, Regula; Klose, Annerose; Beck-Sickinger, Annette G.; Beyermann, Michael (Tetrahedron Letters, 2003)

Nε-(thiaprolyl)-lysine as a handle for site-specific protein conjugation - Van de Vijver, Pieter; Suylen, Dennis; Dirksen, Anouk; Dawson, Philip E.; Hackeng, Tilman M. (Biopolymers, 2010)

Nε-(thiaprolyl)-lysine as a handle for site-specific protein conjugation - Van de Vijver, Pieter; Suylen, Dennis; Dirksen, Anouk; Dawson, Philip E.; Hackeng, Tilman M. (Biopolymers, 2010)

Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins - Wang, Yanxin J.; Szantai-Kis, D. Miklos; Petersson, E. James (Organic & Biomolecular Chemistry, 2016)
Optimized reaction conditions permit selective desulfurization of thiols or deselenization of selenols in the presence of thioamides to enable traceless thioamide incorporation by peptide ligation. , Thioamides are single-atom substitutions of canonical amide bonds, and have been proven to be versatile and minimally perturbing probes in protein folding studies. Previously, our group showed that thioamides can be incorporated into proteins by native chemical ligation (NCL) with Cys as a ligation handle. In this study, we report the expansion of this strategy into non-Cys ligation sites, utilizing radical initiated desulfurization to “erase” the side chain thiol after ligation. The reaction exhibited high chemoselectivity against thioamides, which can be further enhanced with thioacetamide as a sacrificial scavenger. As a proof-of-concept example, we demonstrated the incorporation of a thioamide probe into a 56 amino acid protein, the B1 domain of Protein G (GB1). Finally, we showed that the method can be extended to β-thiol amino acid analogs and selenocysteine.

Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins - Wang, Yanxin J.; Szantai-Kis, D. Miklos; Petersson, E. James (Organic & Biomolecular Chemistry, 2016)
Optimized reaction conditions permit selective desulfurization of thiols or deselenization of selenols in the presence of thioamides to enable traceless thioamide incorporation by peptide ligation. , Thioamides are single-atom substitutions of canonical amide bonds, and have been proven to be versatile and minimally perturbing probes in protein folding studies. Previously, our group showed that thioamides can be incorporated into proteins by native chemical ligation (NCL) with Cys as a ligation handle. In this study, we report the expansion of this strategy into non-Cys ligation sites, utilizing radical initiated desulfurization to “erase” the side chain thiol after ligation. The reaction exhibited high chemoselectivity against thioamides, which can be further enhanced with thioacetamide as a sacrificial scavenger. As a proof-of-concept example, we demonstrated the incorporation of a thioamide probe into a 56 amino acid protein, the B1 domain of Protein G (GB1). Finally, we showed that the method can be extended to β-thiol amino acid analogs and selenocysteine.

Palmitoylated SDF1 α Shows Increased Resistance against Proteolytic Degradation in Liver Homogenates - Bellmann-Sickert, Kathrin; Beck-Sickinger, Annette G. (ChemMedChem, 2011)

Palmitoylated SDF1 α Shows Increased Resistance against Proteolytic Degradation in Liver Homogenates - Bellmann-Sickert, Kathrin; Beck-Sickinger, Annette G. (ChemMedChem, 2011)

Identification of a potential modification site in human stromal cell-derived factor-1 - Baumann, Lars; Beck-Sickinger, Annette G. (Biopolymers, 2010)

Identification of a potential modification site in human stromal cell-derived factor-1 - Baumann, Lars; Beck-Sickinger, Annette G. (Biopolymers, 2010)

Native Chemical Ligation through in Situ O to S Acyl Shift - Botti, Paolo; Villain, Matteo; Manganiello, Sonia; Gaertner, Hubert (Organic Letters, 2004)

Native Chemical Ligation through in Situ O to S Acyl Shift - Botti, Paolo; Villain, Matteo; Manganiello, Sonia; Gaertner, Hubert (Organic Letters, 2004)

Chemically Synthesized SDF-1α Analogue, N33A, Is a Potent Chemotactic Agent for CXCR4/Fusin/LESTR-expressing Human Leukocytes - Ueda, Hirotsugu; Siani, Michael A.; Gong, Wanghua; Thompson, Darren A.; Brown, Garth G.; Wang, Ji Ming (Journal of Biological Chemistry, 1997)

Chemically Synthesized SDF-1α Analogue, N33A, Is a Potent Chemotactic Agent for CXCR4/Fusin/LESTR-expressing Human Leukocytes - Ueda, Hirotsugu; Siani, Michael A.; Gong, Wanghua; Thompson, Darren A.; Brown, Garth G.; Wang, Ji Ming (Journal of Biological Chemistry, 1997)

Rapid and low-cost multiplex synthesis of chemokine analogs - Paolini-Bertrand, Marianne; Cerini, Fabrice; Martins, Elsa; Scurci, Ilaria; Hartley, Oliver (Journal of Biological Chemistry, 2018)

Rapid and low-cost multiplex synthesis of chemokine analogs - Paolini-Bertrand, Marianne; Cerini, Fabrice; Martins, Elsa; Scurci, Ilaria; Hartley, Oliver (Journal of Biological Chemistry, 2018)

Fmoc Synthesis of Peptide Thioesters without Post-Chain-Assembly Manipulation - Zheng, Ji-Shen; Chang, Hao-Nan; Wang, Feng-Liang; Liu, Lei (Journal of the American Chemical Society, 2011)

Total chemical synthesis and high-resolution crystal structure of the potent anti-HIV protein AOP-RANTES - Wilken, Jill; Hoover, David; Thompson, Darren A; Barlow, Paul N; McSparron, Helen; Picard, Laurent; Wlodawer, Alexander; Lubkowski, Jacek; Kent, Stephen BH (Chemistry & Biology, 1999)

Plant Antimicrobial Peptides Snakin-1 and Snakin-2: Chemical Synthesis and Insights into the Disulfide Connectivity - Harris, Paul W. R.; Yang, Sung-Hyun; Molina, Antonio; López, Gemma; Middleditch, Martin; Brimble, Margaret A. (Chemistry - A European Journal, 2014)

Fmoc Synthesis of Peptide Thioesters without Post-Chain-Assembly Manipulation - Zheng, Ji-Shen; Chang, Hao-Nan; Wang, Feng-Liang; Liu, Lei (Journal of the American Chemical Society, 2011)

Elucidation of the Covalent and Tertiary Structures of Biologically Active Ts3 Toxin - Dang, Bobo; Kubota, Tomoya; Mandal, Kalyaneswar; Correa, Ana M.; Bezanilla, Francisco; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2016)

Total chemical synthesis and high-resolution crystal structure of the potent anti-HIV protein AOP-RANTES - Wilken, Jill; Hoover, David; Thompson, Darren A; Barlow, Paul N; McSparron, Helen; Picard, Laurent; Wlodawer, Alexander; Lubkowski, Jacek; Kent, Stephen BH (Chemistry & Biology, 1999)

Plant Antimicrobial Peptides Snakin-1 and Snakin-2: Chemical Synthesis and Insights into the Disulfide Connectivity - Harris, Paul W. R.; Yang, Sung-Hyun; Molina, Antonio; López, Gemma; Middleditch, Martin; Brimble, Margaret A. (Chemistry - A European Journal, 2014)

Engineering and Chemical Synthesis of a Transmembrane Protein: The HCV Protease Cofactor Protein NS4A - Bianchi, Elisabetta; Ingenito, Raffaele; Simon, Reyna J.; Pessi, Antonello (Journal of the American Chemical Society, 1999)

Elucidation of the Covalent and Tertiary Structures of Biologically Active Ts3 Toxin - Dang, Bobo; Kubota, Tomoya; Mandal, Kalyaneswar; Correa, Ana M.; Bezanilla, Francisco; Kent, Stephen B. H. (Angewandte Chemie International Edition, 2016)

Synthesis and Functional Characterization of Tridegin and Its Analogues: Inhibitors and Substrates of Factor XIIIa - Böhm, Miriam; Kühl, Toni; Hardes, Kornelia; Coch, Richard; Arkona, Christoph; Schlott, Bernhard; Steinmetzer, Torsten; Imhof, Diana (ChemMedChem, 2012)

Fmoc-based synthesis of the human CC chemokine CCL14/HCC-1 by SPPS and native chemical ligation - Escher, Sylvia E.; Klüver, Enno; Adermann, Knut (Letters in Peptide Science, 2001)

Chemical Protein Synthesis by Chemoselective α-Ketoacid-Hydroxylamine (KAHA) Ligations with 5-Oxaproline - Pattabiraman, Vijaya R.; Ogunkoya, Ayodele O.; Bode, Jeffrey W. (Angewandte Chemie, 2012)

The E15R Point Mutation in Scorpion Toxin Cn2 Uncouples Its Depressant and Excitatory Activities on Human Na V 1.6 - Israel, Mathilde R.; Thongyoo, Panumart; Deuis, Jennifer R.; Craik, David J.; Vetter, Irina; Durek, Thomas (Journal of Medicinal Chemistry, 2018)

Engineering and Chemical Synthesis of a Transmembrane Protein: The HCV Protease Cofactor Protein NS4A - Bianchi, Elisabetta; Ingenito, Raffaele; Simon, Reyna J.; Pessi, Antonello (Journal of the American Chemical Society, 1999)

Chemical Engineering and Structural and Pharmacological Characterization of the α-Scorpion Toxin OD1 - Durek, Thomas; Vetter, Irina; Wang, Ching-I Anderson; Motin, Leonid; Knapp, Oliver; Adams, David J.; Lewis, Richard J.; Alewood, Paul F. (ACS Chemical Biology, 2013)

Synthesis and Functional Characterization of Tridegin and Its Analogues: Inhibitors and Substrates of Factor XIIIa - Böhm, Miriam; Kühl, Toni; Hardes, Kornelia; Coch, Richard; Arkona, Christoph; Schlott, Bernhard; Steinmetzer, Torsten; Imhof, Diana (ChemMedChem, 2012)

Nickel-Catalyzed Hydroalkenylation of Alkynes through C–F Bond Activation: Synthesis of 2-Fluoro-1,3-dienes - Watabe, Yota; Kanazawa, Kohei; Fujita, Takeshi; Ichikawa, Junji (Synthesis, 2017)
2-Fluoro-1,3-dienes were synthesized through nickel-catalyzed coupling reactions between β,β-difluorostyrenes and alkynes in the presence of ZrF4 as co-catalyst and a hydride source derived from triethylborane and lithium isopropoxide. Mechanistic studies revealed that the carbon–fluorine bond was cleaved by β-fluorine elimination from intermediary nickelacyclopentenes generated through oxidative cyclization of the two substrates.

Fmoc-based synthesis of the human CC chemokine CCL14/HCC-1 by SPPS and native chemical ligation - Escher, Sylvia E.; Klüver, Enno; Adermann, Knut (Letters in Peptide Science, 2001)

Synthesis of (E)-4,5-Dihydro-1H-Pyrazoles via Tandem Intermolecular Addition–Cyclization of N-Propargylic Sulfonylhydrazones - Tang, Hai-Tao; Zeng, Jia-Hao; Chen, Jun-Jia; Chen, Yi-Hui; Zhan, Zhuang-Ping (Synlett, 2017)
A new strategy for the synthesis of (E)-4-benzylidene-4,5-dihydro-1H-pyrazoles through tandem intermolecular addition–intramolecular cyclization of N-propargylic sulfonylhydrazones has been developed. In this study, we firstly report that N-propargylic sulfonylhydrazones react with electrophilic reagents to afford 4-substituted pyrazole derivatives.

Chemical Protein Synthesis by Chemoselective α-Ketoacid-Hydroxylamine (KAHA) Ligations with 5-Oxaproline - Pattabiraman, Vijaya R.; Ogunkoya, Ayodele O.; Bode, Jeffrey W. (Angewandte Chemie, 2012)

The E15R Point Mutation in Scorpion Toxin Cn2 Uncouples Its Depressant and Excitatory Activities on Human Na V 1.6 - Israel, Mathilde R.; Thongyoo, Panumart; Deuis, Jennifer R.; Craik, David J.; Vetter, Irina; Durek, Thomas (Journal of Medicinal Chemistry, 2018)

Development of Powerful Auxiliary-Mediated Ligation To Facilitate Rapid Protein Assembly - Yin, Hongli; Lu, Dan; Wang, Siyao; Wang, Ping (Organic Letters, 2019)

Chemical Engineering and Structural and Pharmacological Characterization of the α-Scorpion Toxin OD1 - Durek, Thomas; Vetter, Irina; Wang, Ching-I Anderson; Motin, Leonid; Knapp, Oliver; Adams, David J.; Lewis, Richard J.; Alewood, Paul F. (ACS Chemical Biology, 2013)

The chemical synthesis of the GstI protein by NCL on a X-Met site - Saporito, Angela; Marasco, Daniela; Chambery, Angela; Botti, Paolo; Monti, Simona M.; Pedone, Carlo; Ruvo, Menotti (Biopolymers, 2006)

Nickel-Catalyzed Hydroalkenylation of Alkynes through C–F Bond Activation: Synthesis of 2-Fluoro-1,3-dienes - Watabe, Yota; Kanazawa, Kohei; Fujita, Takeshi; Ichikawa, Junji (Synthesis, 2017)
2-Fluoro-1,3-dienes were synthesized through nickel-catalyzed coupling reactions between β,β-difluorostyrenes and alkynes in the presence of ZrF4 as co-catalyst and a hydride source derived from triethylborane and lithium isopropoxide. Mechanistic studies revealed that the carbon–fluorine bond was cleaved by β-fluorine elimination from intermediary nickelacyclopentenes generated through oxidative cyclization of the two substrates.

Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis: Preparation of Peptide Thioesters - Miyajima, Rin; Tsuda, Yusuke; Inokuma, Tsubasa; Shigenaga, Akira; Imanishi, Miki; Futaki, Shiroh; Otaka, Akira (Biopolymers, 2016)

Synthesis of (E)-4,5-Dihydro-1H-Pyrazoles via Tandem Intermolecular Addition–Cyclization of N-Propargylic Sulfonylhydrazones - Tang, Hai-Tao; Zeng, Jia-Hao; Chen, Jun-Jia; Chen, Yi-Hui; Zhan, Zhuang-Ping (Synlett, 2017)
A new strategy for the synthesis of (E)-4-benzylidene-4,5-dihydro-1H-pyrazoles through tandem intermolecular addition–intramolecular cyclization of N-propargylic sulfonylhydrazones has been developed. In this study, we firstly report that N-propargylic sulfonylhydrazones react with electrophilic reagents to afford 4-substituted pyrazole derivatives.

Extending Synthetic Access to Proteins with a Removable Acyl Transfer Auxiliary - Offer, John; Boddy, C. N. C.; Dawson, Philip E. (Journal of the American Chemical Society, 2002)

Synthesis of Cysteine-Rich Peptides by Native Chemical Ligation without Use of Exogenous Thiols - Tsuda, Shugo; Yoshiya, Taku; Mochizuki, Masayoshi; Nishiuchi, Yuji (Organic Letters, 2015)

Development of Powerful Auxiliary-Mediated Ligation To Facilitate Rapid Protein Assembly - Yin, Hongli; Lu, Dan; Wang, Siyao; Wang, Ping (Organic Letters, 2019)

Internal Activation of Peptidyl Prolyl Thioesters in Native Chemical Ligation - Gui, Yue; Qiu, Lingqi; Li, Yaohao; Li, Hongxing; Dong, Suwei (Journal of the American Chemical Society, 2016)

The chemical synthesis of the GstI protein by NCL on a X-Met site - Saporito, Angela; Marasco, Daniela; Chambery, Angela; Botti, Paolo; Monti, Simona M.; Pedone, Carlo; Ruvo, Menotti (Biopolymers, 2006)

Probing intermolecular backbone H-bonding in serine proteinase-protein inhibitor complexes - Lu, Wuyuan; Randal, Michael; Kossiakoff, Anthony; Kent, Stephen B.H. (Chemistry & Biology, 1999)

Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis: Preparation of Peptide Thioesters - Miyajima, Rin; Tsuda, Yusuke; Inokuma, Tsubasa; Shigenaga, Akira; Imanishi, Miki; Futaki, Shiroh; Otaka, Akira (Biopolymers, 2016)

Extending Synthetic Access to Proteins with a Removable Acyl Transfer Auxiliary - Offer, John; Boddy, C. N. C.; Dawson, Philip E. (Journal of the American Chemical Society, 2002)

Synthesis of Cysteine-Rich Peptides by Native Chemical Ligation without Use of Exogenous Thiols - Tsuda, Shugo; Yoshiya, Taku; Mochizuki, Masayoshi; Nishiuchi, Yuji (Organic Letters, 2015)

An investigation of the role of the adiponectin variable domain on the stability of the collagen-like domain: The Role of the Adiponectin Variable Domain - Harris, Paul W. R.; Hampe, Lutz; Radjainia, Mazdak; Brimble, Margaret A.; Mitra, Alok K. (Biopolymers, 2014)

Internal Activation of Peptidyl Prolyl Thioesters in Native Chemical Ligation - Gui, Yue; Qiu, Lingqi; Li, Yaohao; Li, Hongxing; Dong, Suwei (Journal of the American Chemical Society, 2016)

Total Synthesis of Homogeneous Variants of Hirudin P6: A Post-Translationally Modified Anti-Thrombotic Leech-Derived Protein - Hsieh, Yves S. Y.; Wijeyewickrema, Lakshmi C.; Wilkinson, Brendan L.; Pike, Robert N.; Payne, Richard J. (Angewandte Chemie International Edition, 2014)

Probing intermolecular backbone H-bonding in serine proteinase-protein inhibitor complexes - Lu, Wuyuan; Randal, Michael; Kossiakoff, Anthony; Kent, Stephen B.H. (Chemistry & Biology, 1999)

Chemical synthesis of kurtoxin, a T-type calcium channel blocker - Nishio, Hideki; Nishiuchi, Yuji; Ishimaru, Masanori; Kimura, Terutoshi (International Journal of Peptide Research and Therapeutics, 2003)

Immobilization methods for the rapid total chemical synthesis of proteins on microtiter plates: Rapid Chemical Synthesis of Proteins on Microtiter Plates - Zitterbart, Robert; Krumrey, Michael; Seitz, Oliver (Journal of Peptide Science, 2017)

An investigation of the role of the adiponectin variable domain on the stability of the collagen-like domain: The Role of the Adiponectin Variable Domain - Harris, Paul W. R.; Hampe, Lutz; Radjainia, Mazdak; Brimble, Margaret A.; Mitra, Alok K. (Biopolymers, 2014)

Fulditoxin, representing a new class of dimeric snake toxins, defines novel pharmacology at nicotinic ACh receptors - Foo, Chun Shin; Jobichen, Chacko; Hassan‐Puttaswamy, Varuna; Dekan, Zoltan; Tae, Han‐Shen; Bertrand, Daniel; Adams, David J.; Alewood, Paul F.; Sivaraman, J.; Nirthanan, Selvanayagam; Kini, R. Manjunatha (British Journal of Pharmacology, 2020)

Total Synthesis of Homogeneous Variants of Hirudin P6: A Post-Translationally Modified Anti-Thrombotic Leech-Derived Protein - Hsieh, Yves S. Y.; Wijeyewickrema, Lakshmi C.; Wilkinson, Brendan L.; Pike, Robert N.; Payne, Richard J. (Angewandte Chemie International Edition, 2014)

Chemical synthesis and biotinylation of the thrombospondin domain TSR2 - Tiefenbrunn, Theresa K.; Dawson, Philip E. (Protein Science, 2009)

Chemical synthesis of kurtoxin, a T-type calcium channel blocker - Nishio, Hideki; Nishiuchi, Yuji; Ishimaru, Masanori; Kimura, Terutoshi (International Journal of Peptide Research and Therapeutics, 2003)

Automated Fmoc-Based Solid-Phase Synthesis of Peptide Thioesters with Self-Purification Effect and Application in the Construction of Immobilized SH3 Domains - Mende, Franziska; Beisswenger, Michael; Seitz, Oliver (Journal of the American Chemical Society, 2010)

Immobilization methods for the rapid total chemical synthesis of proteins on microtiter plates: Rapid Chemical Synthesis of Proteins on Microtiter Plates - Zitterbart, Robert; Krumrey, Michael; Seitz, Oliver (Journal of Peptide Science, 2017)

Construction of Challenging Proline–Proline Junctions via Diselenide–Selenoester Ligation Chemistry - Sayers, Jessica; Karpati, Phillip M. T.; Mitchell, Nicholas J.; Goldys, Anna M.; Kwong, Stephen M.; Firth, Neville; Chan, Bun; Payne, Richard J. (Journal of the American Chemical Society, 2018)

Fulditoxin, representing a new class of dimeric snake toxins, defines novel pharmacology at nicotinic ACh receptors - Foo, Chun Shin; Jobichen, Chacko; Hassan‐Puttaswamy, Varuna; Dekan, Zoltan; Tae, Han‐Shen; Bertrand, Daniel; Adams, David J.; Alewood, Paul F.; Sivaraman, J.; Nirthanan, Selvanayagam; Kini, R. Manjunatha (British Journal of Pharmacology, 2020)

Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation–Desulfurization Chemistry - Malins, Lara R.; Giltrap, Andrew M.; Dowman, Luke J.; Payne, Richard J. (Organic Letters, 2015)

Chemical synthesis and biotinylation of the thrombospondin domain TSR2 - Tiefenbrunn, Theresa K.; Dawson, Philip E. (Protein Science, 2009)

Rapid assembly and profiling of an anticoagulant sulfoprotein library - Watson, Emma E.; Ripoll-Rozada, Jorge; Lee, Ashley C.; Wu, Mike C. L.; Franck, Charlotte; Pasch, Tim; Premdjee, Bhavesh; Sayers, Jessica; Pinto, Maria F.; Martins, Pedro M.; Jackson, Shaun P.; Pereira, Pedro José Barbosa; et al. (Proceedings of the National Academy of Sciences, 2019)
Hematophagous organisms produce a suite of salivary proteins which interact with the host’s coagulation machinery to facilitate the acquisition and digestion of a bloodmeal. Many of these biomolecules inhibit the central blood-clotting serine proteinase thrombin that is also the target of several clinically approved anticoagulants. Here a bioinformatics approach is used to identify seven tick proteins with putative thrombin inhibitory activity that we predict to be posttranslationally sulfated at two conserved tyrosine residues. To corroborate the biological role of these molecules and investigate the effects of amino acid sequence and sulfation modifications on thrombin inhibition and anticoagulant activity, a library of 34 homogeneously sulfated protein variants were rapidly assembled using one-pot diselenide-selenoester ligation (DSL)-deselenization chemistry. Downstream functional characterization validated the thrombin-directed activity of all target molecules and revealed that posttranslational sulfation of specific tyrosine residues crucially modulates potency. Importantly, access to this homogeneously modified protein library not only enabled the determination of key structure–activity relationships and the identification of potent anticoagulant leads, but also revealed subtleties in the mechanism of thrombin inhibition, between and within the families, that would be impossible to predict from the amino acid sequence alone. The synthetic platform described here therefore serves as a highly valuable tool for the generation and thorough characterization of libraries of related peptide and/or protein molecules (with or without modifications) for the identification of lead candidates for medicinal chemistry programs.

Automated Fmoc-Based Solid-Phase Synthesis of Peptide Thioesters with Self-Purification Effect and Application in the Construction of Immobilized SH3 Domains - Mende, Franziska; Beisswenger, Michael; Seitz, Oliver (Journal of the American Chemical Society, 2010)

Construction of Challenging Proline–Proline Junctions via Diselenide–Selenoester Ligation Chemistry - Sayers, Jessica; Karpati, Phillip M. T.; Mitchell, Nicholas J.; Goldys, Anna M.; Kwong, Stephen M.; Firth, Neville; Chan, Bun; Payne, Richard J. (Journal of the American Chemical Society, 2018)