Petasis-mediated exo-iminoglycals synthesis from glyconolactams allows access to unprecedented 1-spirocyclopropyl deoxynojirimycin

IF 3.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2026-02-01 Epub Date: 2025-12-03 DOI:10.1016/j.carres.2025.109765

Lilou Chopin , Aurélien Beato , Dylan Yorga , Nicolas Auberger , Jean-Bernard Behr , Jérôme Désiré , Yves Blériot

引用次数: 0

Abstract

We report herein the olefination of a set of six N-Boc glyconolactams using Petasis reagent to yield unprecedented exoiminoglycals. In addition, a modified Simmons-Smith cyclopropanation was successfully applied to the D-gluco-configured olefin to furnish the unprecedented 1-spirocyclic deoxynojirimycin which proved to be a poor inhibitor of glycosidases in its unprotected form.

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由糖醇内酯合成的petasis介导的外亚氨基糖可以获得前所未有的1-螺环丙基脱氧诺吉霉素

我们在此报告了一组六N-Boc糖内酯的烯烃使用Petasis试剂产生前所未有的外亚胺糖。此外，对d -葡萄糖构型的烯烃进行了改良的西蒙斯-史密斯环丙烷化反应，得到了前所未有的1-螺环脱氧诺吉霉素，该霉素在无保护形式下是一种较差的糖苷酶抑制剂。

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

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".