A concise synthetic approach for isoiminosugars

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-08-10 DOI:10.1016/j.carres.2024.109239

Martin Thonhofer , André Culum , Tobias Dorn , Roland Fischer , Herwig Prasch , Arnold E. Stütz , Patrick Weber , Tanja M. Wrodnigg

引用次数: 0

Abstract

Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple d-glucopyranoside.

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异亚氨基糖的简明合成方法

异亚氨基糖是具有高度生物活性的物质。在此，我们报告了这一类化合物的简明合成方法。关键步骤依赖于 O-2 对甲苯磺酰化吡喃糖苷中的 1,2-酸酐的立体特异性转变，从而生成 C-2 支链的糖呋喃糖苷。这种方法可以从简单的 d-吡喃葡萄糖苷开始，通过 4 个步骤合成强效 β-半乳糖苷酶抑制剂 4-表异法哥明。

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".