Convergent synthesis of steviol glycosides rebaudioside a and M

IF 2.5 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Carbohydrate Research Pub Date : 2025-03-06 DOI:10.1016/j.carres.2025.109446
Yuanyuan Li , Haoru Zhuang , Xuerui Tao , Yingguo Liu , Tianlu Li , Peng Peng
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Abstract

Steviol glycosides, a natural health-focused sweetener, is receiving increasing attention. Herein, an efficient and concise approach for the convergent synthesis of Rebaudioside A and M has been devised. This method features a AuCl3-tBuCN cooperative catalysis to achieve highly 1, 2-trans stereoselective glycosidation of a C2-branched trisaccharide trichloroacetimidate with tertiary C-13 hydroxy group in steviol aglycone, without relying on neighboring group participation.

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甜菊糖苷雷鲍迪甙a和M的聚合合成
甜菊醇糖苷是一种以健康为重点的天然甜味剂,正受到越来越多的关注。本文设计了一种高效、简便的雷鲍迪苷A和M的聚合合成方法。该方法采用AuCl3-tBuCN协同催化,在不依赖邻基参与的情况下,实现了与甜菊醇苷元中C-13叔羟基的c2支链三氯乙酸三糖的高度1,2 -反式立体选择性糖基化。
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来源期刊
Carbohydrate Research
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".
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