Gold-mediated selective cysteine modification of peptides using allenes

被引:38
作者
Chan, Anna On-Yee [1 ,2 ]
Tsai, Johnson Lui-Lui [1 ,2 ]
Lo, Vanessa Kar-Yan [1 ,2 ]
Li, Gai-Li [3 ]
Wong, Man-Kin [3 ]
Che, Chi-Ming [1 ,2 ]
机构
[1] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Open Lab Chem Biol, Hong Kong, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
关键词
CONVERGENT CHEMICAL-SYNTHESIS; POSTTRANSLATIONAL MODIFICATIONS; HIGHLY EFFICIENT; AQUEOUS-MEDIUM; ALLYLIC SELENOSULFIDE; RHODIUM CARBENOIDS; AMIDE SYNTHESIS; PROTEINS; LIGATION; CHEMISTRY;
D O I
10.1039/c2cc38214h
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
A new approach for selective modification of cysteine-containing peptides through gold-mediated oxidative allene-thiol coupling reaction in aqueous medium is developed.
引用
收藏
页码:1428 / 1430
页数:3
相关论文
共 62 条
[1]
Chemoselectivity and the Curious Reactivity Preferences of Functional Groups [J].
Afagh, Nicholas A. ;
Yudin, Andrei K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) :262-310
[2]
[Anonymous], 2005, POSTTRANSLATIONAL MO
[3]
Selective tryptophan modification with rhodium carbenoids in aqueous solution [J].
Antos, JM ;
Francis, MB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10256-10257
[4]
Transition metal catalyzed methods for site-selective protein modification [J].
Antos, John M. ;
Francis, Matthew B. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (03) :253-262
[5]
Chemoselective Tryptophan Labeling with Rhodium Carbenoids at Mild pH [J].
Antos, John M. ;
McFarland, Jesse M. ;
Iavarone, Anthony T. ;
Francis, Matthew B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6301-6308
[6]
Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[7]
Kinetically controlled ligation for the convergent chemical synthesis of proteins [J].
Bang, Duhee ;
Pentelute, Brad L. ;
Kent, Stephen B. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3985-3988
[8]
Protein Chemical Modification on Endogenous Amino Acids [J].
Basle, Emmanuel ;
Joubert, Nicolas ;
Pucheault, Mathieu .
CHEMISTRY & BIOLOGY, 2010, 17 (03) :213-227
[9]
Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins [J].
Bernardes, Goncalo J. L. ;
Chalker, Justin M. ;
Errey, James C. ;
Davis, Benjamin G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5052-+
[10]
Golden opportunities in stereoselective catalysis [J].
Bongers, Nadine ;
Krause, Norbert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2178-2181