Gold-mediated selective cysteine modification of peptides using allenes

被引：35

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

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 14期

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：

0703 ;

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

页码：1428 / 1430

页数：3

共 62 条

[41] Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation
McFarland, JM
Francis, MB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) : 13490 - 13491
[42] The first gold-catalyzed C-S bond formation:: Cycloisomerization of α-thioallenes to 2,5-dihydrothiophenes
Morita, N
Krause, N
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) : 1897 - 1899
[43] Transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles: a perspective
Munoz, Maria Paz
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) : 3584 - 3594
[44] Proximity-driven metallopeptide catalysis: Remarkable side-chain scope enables modification of the Fos bZip domain
Popp, Brian V.
Ball, Zachary T.
[J]. CHEMICAL SCIENCE, 2011, 2 (04) : 690 - 695
[45] Structure-Selective Modification of Aromatic Side Chains with Dirhodium Metallopeptide Catalysts
Popp, Brian V.
Ball, Zachary T.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) : 6660 - +
[46] Chemistry in living systems
Prescher, JA
Bertozzi, CR
[J]. NATURE CHEMICAL BIOLOGY, 2005, 1 (01) : 13 - 21
[47] Generation of new enzymes via covalent modification of existing proteins
Qi, DF
Tann, CM
Haring, D
Distefano, MD
[J]. CHEMICAL REVIEWS, 2001, 101 (10) : 3081 - 3111
[48] Postsynthetic Modification of Peptides: Chemoselective C-Arylation of Tryptophan Residues
Ruiz-Rodriguez, Javier
Albericio, Fernando
Lavilla, Rodolfo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (04) : 1124 - 1127
[49] Electron-Deficient Alkynes as Cleavable Reagents for the Modification of Cysteine-Containing Peptides in Aqueous Medium
Shiu, Hoi-Yan
Chan, Tak-Chung
Ho, Chi-Ming
Liu, Yungen
Wong, Man-Kin
Che, Chi-Ming
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) : 3839 - 3850
[50] Synthesis of ketene (S, Te)acetals and their transformation into Z-α-phenylthio-α,β-unsaturated aldehydes
Silveira, CC
Perin, G
Braga, AL
Dabdoub, MJ
Jacob, RG
[J]. TETRAHEDRON, 1999, 55 (24) : 7421 - 7432

← 1 2 3 4 5 6 7 →