Photo-induced glycosylation using edible polyphenol ellagic acid

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-03-17 DOI:10.1016/j.carres.2025.109461

Hidenari Shigeta, Satomi Goi, Daisuke Takahashi, Kazunobu Toshima

引用次数: 0

Abstract

Photo-induced glycosylation reactions of trichloroacetoimidate donors with alcohol acceptors were investigated under visible light (470 nm) irradiation using the edible polyphenol, ellagic acid. We found, for the first time, that these glycosylations proceeded smoothly under mild reaction conditions, and the corresponding glycosides were obtained in high yields. Furthermore, this glycosylation method was applicable to a wide range of trichloroacetimidate donors and alcohol acceptors, and showed high chemoselectivity over glycosyl phosphate, fluoride, glycal, thioglycoside, and (N-phenyl)trifluoroacetimidate.

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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".