Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C-H bond functionalization

被引：208

作者：

Zhao, Liang ^{[1
]}

Basle, Oliver ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2009年 / 106卷 / 11期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

amino acid; C-C bond formation; peptide modification; PHASE-TRANSFER CATALYSIS; ALPHA-ARYLATION; AMINO-ACIDS; TERMINAL FUNCTIONALIZATION; NITROGEN ATOM; ESTERS; ANTIBIOTICS; VANCOMYCIN; ADJACENT; ALKYNYLATION;

D O I：

10.1073/pnas.0809052106

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A copper-catalyzed alpha-functionalization of glycine derivatives and short peptides with nucleophiles is described. The present method provides ways to introduce functionalities such as aryl, vinyl, alkynyl, or indolyl specifically to the terminal glycine moieties of small peptides, which are normally difficult in peptide modifications. Furthermore, on functionalization, the configurations of other stereocenters in the peptides could be maintained. Because the functionalized peptides could easily be deprotected and carried onto the next coupling process, our approach provides a useful tool for the peptide-based biological research.

引用

页码：4106 / 4111

页数：6

共 42 条

[1] METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].