Recent Advances in Chemical Protein Modification via Cysteine

被引:8
作者
Wang Changliu [1 ]
Zhao Yongli [1 ]
Zhao Junfeng [2 ]
机构
[1] Jiangxi Normal Univ, Natl Res Centerfor Carbohydrate Synth, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
[2] Guangzhou Med Univ, Sch Pharmaceut Sci, State Key Lab Resp Dis, Guangzhou 511436, Peoples R China
基金
中国国家自然科学基金;
关键词
peptide modification; chemical protein modification; cysteine; CONTAINING PEPTIDES; DRUG CONJUGATE; CHEMISTRY; REAGENTS; ALKYNYLATION; PALLADIUM; THIOLS; SITE; BIOCONJUGATION;
D O I
10.6023/cjoc202203008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Proteins are the most abundant biomolecules in nature and are involved almost in all living processes. Chemical modification of proteins is an efficient strategy to mediate and study the physical and chemical properties and biological functionalities of proteins. Most protein chemical modifications are based on the bioorthogonal reactivities of the side chain functional groups of certain amino acid residues. Among 20 proteinogenic amino acids, cysteine has become the best choice for chemical protein modification, owning to its relative low abundance in proteins, the unique nucleophilicity and low redox potential of its mercaptan group. The recent advances in chemical protein modification via cysteine are comprehensively reviewed and the challenges and applications for future development are discussed.
引用
收藏
页码:2774 / 2792
页数:19
相关论文
共 108 条
[1]   Allenamides as Orthogonal Handles for Selective Modification of Cysteine in Peptides and Proteins [J].
Abbas, Ata ;
Xing, Bengang ;
Loh, Teck-Peng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7491-7494
[2]   Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents [J].
Abegg, Daniel ;
Frei, Reto ;
Cerato, Luca ;
Hari, Durga Prasad ;
Wang, Chao ;
Waser, Jerome ;
Adibekian, Alexander .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) :10852-10857
[3]   Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization [J].
Allouche, Emmanuelle M. D. ;
Grinhagena, Elija ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (07)
[4]  
[Anonymous], 2022, CHINESE J ORG CHEM, V42, P2774
[5]   Site-Specific Dual Functionalization of Cysteine Residue in Peptides and Proteins with 2-Azidoacrylates [J].
Ariyasu, Shinya ;
Hayashi, Hirohito ;
Xing, Bengang ;
Chiba, Shunsuke .
BIOCONJUGATE CHEMISTRY, 2017, 28 (04) :897-902
[6]   Chemoselective protection of thiols versus alcohols and phenols. The Tosvinyl group [J].
Arjona, O ;
Medel, R ;
Rojas, J ;
Costa, AM ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 2003, 44 (34) :6369-6373
[7]   p-toluenesulfonylacetylene as thiol protecting group [J].
Arjona, O ;
Iradier, F ;
Medel, R ;
Plumet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6090-6093
[8]   Selective and reversible photochemical derivatization of cysteine residues in peptides and proteins [J].
Arumugam, Selvanathan ;
Guo, Jun ;
Mbua, Ngalle Eric ;
Friscourt, Frederic ;
Lin, Nannan ;
Nekongo, Emmanuel ;
Boons, Geert-Jan ;
Popik, Vladimir V. .
CHEMICAL SCIENCE, 2014, 5 (04) :1591-1598
[9]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[10]   Late-Stage Peptide Macrocyclization by Palladium-Catalyzed Site-Selective C-H Olefination of Tryptophan [J].
Bai, Zengbing ;
Cai, Chuangxu ;
Sheng, Wangjian ;
Ren, Yuxiang ;
Wang, Huan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (34) :14686-14692