A Novel, Industrially-feasible Synthetic Route to (+)-Biotin from L-Cysteine

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-06-20 DOI:10.1002/hlca.202400090

Qiongmei Zhang, Kun Peng, Werner Bonrath, Zili Zhang, Zhibin Zhu, Yuehan Xing, Xiaoyan Wang, Bo Gao, Jonathan A. Medlock

引用次数: 0

Abstract

A novel, industrially viable synthetic route to (+)-biotin has been developed starting from L-cysteine via the known key thiolactone intermediate. The route takes advantage of the in-built stereochemistry of the cysteine starting material and the best features of the two current industrialized processes. The key transformations are the conversion of L-cysteine into a hydantoin avoiding racemization followed by catalytic cyanation and thiolactonization to form the required thiolactone intermediate. This known intermediate can be readily further transformed into (+)-biotin.

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从 L-半胱氨酸合成 (+)- 生物素的新颖、工业上可行的合成路线

以 L-半胱氨酸为起点，通过已知的关键硫内酯中间体，我们开发出了一种新型的、具有工业可行性的 (+)- 生物素合成路线。该路线利用了半胱氨酸起始原料的固有立体化学特性以及当前两种工业化工艺的最佳特点。关键的转化过程是将 L-半胱氨酸转化为海因，避免外消旋化，然后进行催化氰化和硫代内酰化，形成所需的硫代内酯中间体。这种已知的中间体很容易进一步转化为 (+)- 生物素。

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

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.