Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

被引：13

作者：

Wu, Huabin ^{[1
]}

Handoko ^{[1
]}

Raj, Monika ^{[1
,2
]}

Arora, Paramjit S. ^{[1
]}

机构：

[1] NYU, Dept Chem, 100 Washington Sq East, New York, NY 10003 USA

[2] Auburn Univ, Dept Chem & Biochem, Auburn, AL 36830 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

基金：

美国国家科学基金会;

关键词：

NATIVE CHEMICAL LIGATION; ACYL TRANSFER; CARBOXYLIC-ACIDS; TRANSESTERIFICATION; ORGANOCATALYSIS; ALCOHOLS; THIOLS; ESTER;

D O I：

10.1021/acs.orglett.7b02412

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, the design of a catalyst that combines lessons learned from peptide biosynthesis, enzymes, and organocatalysts is described. The catalyst features a urea scaffold for carbonyl recognition and elements of nucleophilic catalysis. In the presence of 40 mol % of the organocatalyst, the rate of peptide bond formation is accelerated by 10000 fold over the uncatalyzed reaction between Fmoc-amino acid thioesters and amino acid methyl esters.

引用

页码：5122 / 5125

页数：4

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