Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones

被引：10

作者：

Brun, Omar ^{[1
]}

Agramunt, Jordi ^{[1
]}

Raich, Lluis ^{[1
,2
]}

Rovira, Carme ^{[1
,2
,4
]}

Pedroso, Enrique ^{[1
,3
]}

Grandas, Anna ^{[1
,3
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Inorgan & Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[2] Univ Barcelona, Fac Quim, IQTCUB, Seccio Q Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[3] Univ Barcelona, Fac Quim, IBUB, Seccio Q Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[4] ICREA, Passeig Lluis Co 23, Barcelona 08010, Spain

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

SITE-SPECIFIC CONJUGATION; FLUORESCENT-PROBE; HOMOCYSTEINE; PROTEINS; OLIGONUCLEOTIDES; GLUTATHIONE; STABILITY; PEPTIDES; REAGENTS; BIOCONJUGATION;

D O I：

10.1021/acs.orglett.6b02301

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.

引用

页码：4836 / 4839

页数：4

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