Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids

被引：24

作者：

Brown, Zachary Z. ^{[2
]}

Schafmeister, Christian E. ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

BETA-PEPTIDES; FOLDAMERS; REQUIREMENTS; SCAFFOLDS; OLIGOMERS; MIMETICS; PROTEINS; FIELD;

D O I：

10.1021/ol100048g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Steric hindrance assists in the formation of hindered diketopiperazines using acyl-transfer coupling. In acyl-transfer coupling, the carboxylate of an unprotected N-alkylamino acid attacks an active ester to form a transient anhydride that undergoes an O,N acyl transfer to form a tertiary amide. If the active ester is part of an N-alkylamino acid it will form a diketopiperazine. It is demonstrated here that acyl-transfer coupling can assemble highly functionalized bis-peptides bearing a functional group on every monomer.

引用

页码：1436 / 1439

页数：4

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