立体选择性化学酶级联反应合成密集功能化亚氨基糖

IF 15.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2025-02-10 DOI:10.1021/jacs.4c16732

Christopher R. B. Swanson, Léa Gourbeyre, Grayson J. Ford, Pere Clapés, Sabine L. Flitsch

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引用次数: 0

摘要

1,4-二羰基是构建多种药物载体和天然产物的多功能合成物。然而，立体选择性合成密集功能化1,4-二羰基是具有挑战性的。在这里，我们报道了一种多用途的生物催化途径，利用d-果糖-6-磷酸醛缩酶（EcFSA）以高产量和高达克级的速度获得手性2,3-二羟基-1,4-二酮。这些化合物作为合子的效用在酶级联反应中得到例证，随后的区域和立体选择性酶转氨化反应形成密集功能化的同手性1-吡咯啉，然后化学或酶还原为四取代吡咯烷。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Stereoselective Chemoenzymatic Cascades for the Synthesis of Densely Functionalized Iminosugars

查看原文本刊更多论文

Stereoselective Chemoenzymatic Cascades for the Synthesis of Densely Functionalized Iminosugars

1,4-Dicarbonyls are versatile synthons for the construction of diverse pharmacophores and natural products. However, the stereoselective synthesis of densely functionalized 1,4-dicarbonyls is challenging. Here, we report a versatile biocatalytic route to access chiral 2,3-dihydroxy-1,4-diketones in high yields and up to gram scale using d-fructose-6-phosphate aldolase (EcFSA). The utility of these compounds as synthons is exemplified in enzyme cascades with subsequent regio- and stereoselective enzymatic transamination to form densely functionalized homochiral 1-pyrrolines followed by chemical or enzymatic reduction to tetrasubstituted pyrrolidines.

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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.