Cyclometalated gold(III) complexes for chemoselective cysteine modification via ligand controlled C-S bond-forming reductive elimination

被引：92
作者：
Kung, Karen Ka-Yan
Ko, Hok-Ming
Cui, Jian-Fang
Chong, Hiu-Chi
Leung, Yun-Chung [1 ]
Wong, Man-Kin
机构：
[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 80期
关键词：
SELECTIVE PROTEIN MODIFICATION; AQUEOUS-MEDIUM; ORGANOGOLD(III) COMPLEXES; PEPTIDES; CATALYSIS; GOLD; REARRANGEMENTS; CHEMISTRY; MECHANISM; REAGENTS;
D O I：
10.1039/c4cc04467c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Modular assembly of cyclometalated gold(III) complexes by choosing appropriate bidentate C, N-donor ligands and ancillary ligands for chemoselective cysteine modification of peptides and proteins via C-S bond-forming reductive elimination has been achieved.
引用
收藏
页码：11899 / 11902
页数：4
相关论文
共 38 条
[1]   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
[2]   From disulfide- to thioether-linked glycoproteins [J].
Bernardes, Goncalo J. L. ;
Grayson, Elizabeth J. ;
Thompson, Sam ;
Chalker, Justin M. ;
Errey, James C. ;
El Oualid, Farid ;
Claridge, Timothy D. W. ;
Davis, Benjamin G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2244-2247
[3]   A "Tag-and-Modify" Approach to Site-Selective Protein Modification [J].
Chalker, Justin M. ;
Bernardes, Goncalo J. L. ;
Davis, Benjamin G. .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (09) :730-741
[4]   Chemical Modification of Proteins at Cysteine: Opportunities in Chemistry and Biology [J].
Chalker, Justin M. ;
Bernardes, Goncalo J. L. ;
Lin, Yuya A. ;
Davis, Benjamin G. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (05) :630-640
[5]   Gold-mediated selective cysteine modification of peptides using allenes [J].
Chan, Anna On-Yee ;
Tsai, Johnson Lui-Lui ;
Lo, Vanessa Kar-Yan ;
Li, Gai-Li ;
Wong, Man-Kin ;
Che, Chi-Ming .
CHEMICAL COMMUNICATIONS, 2013, 49 (14) :1428-1430
[6]   Modification of N-Terminal α-Amino Groups of Peptides and Proteins Using Ketenes [J].
Chan, Anna On-Yee ;
Ho, Chi-Ming ;
Chong, Hiu-Chi ;
Leung, Yun-Chung ;
Huang, Jie-Sheng ;
Wong, Man-Kin ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2589-2598
[7]   Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium [J].
Chan, Wing-Kei ;
Ho, Chi-Ming ;
Wong, Man-Kin ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14796-14797
[8]   Dechalcogenative allylic selenosulfide and disulfide rearrangements: Complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media [J].
Crich, David ;
Krishnamurthy, Venkataramanan ;
Brebion, Franck ;
Karatholuvhu, Maheswaran ;
Subramanian, Venkataraman ;
Hutton, Thomas K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10282-10294
[9]   Sigmatropic rearrangements as tools for amino acid and peptide modification: Application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates [J].
Crich, David ;
Zou, Yekui ;
Brebion, Franck .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9172-9177
[10]   Gold catalysis: The benefits of N and N,O ligands [J].
Hashmi, ASK ;
Weyrauch, JP ;
Rudolph, M ;
Kurpejovic, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) :6545-6547
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