In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

IF 14.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2011-08-16 DOI:10.1021/ja2065158

Wenting Wu, Zhihui Zhang, Lanny S. Liebeskind*

引用次数: 54

Abstract

The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

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使用硅致开关的原位羧基活化:酰胺和肽结构的新方法

描述了o -硅基硫酯与胺亲核试剂产生氧酰胺(而不是硫酰胺)的新反应性。直接的第一代三甲基硅基化方案使用双三甲基硅基乙酰胺(BSA)结合o -硅基硫酯对1°和2°胺的独特反应性生成氧酰胺，提供了在中性ph下激活硫醇酸以形成肽键的最简单方法。观察到良好的立体保留。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.

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