Sialylation reactions: Expanding the C-5 effect to phosphate leaving groups.

IF 2.4 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
Carbohydrate Research Pub Date : 2025-02-01 Epub Date: 2024-12-13 DOI:10.1016/j.carres.2024.109353
Anupama Das, Shay Adio, Jeremy Brincken, Alexei V Demchenko, Cristina De Meo
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引用次数: 0

Abstract

With the expanding use of phosphates as leaving groups in sialylations, little remains known about the C-5 effect towards their reactivity and stereoselectivity in the presence of a range of acceptors, and in different solvents. Herein we report the comparison between sialyl phosphate donors bearing N-acetyloxazolidinone and trifluoroacetamido functionalities at C-5. Excellent results and complete stereoselectivity were observed in several sialylations, but the outcome was influenced by the nature of the solvent and/or glycosyl acceptor.

酰化反应:将 C-5 效应扩展到磷酸离去基团。
随着磷酸盐在唾液化反应中作为离去基的使用越来越广泛,在一系列受体和不同溶剂中,C-5对其反应性和立体选择性的影响仍然知之甚少。在此,我们报告了在C-5上具有n -乙酰氯唑烷酮和三氟乙酰胺官能团的唾液酰磷酸盐供体的比较。在几种唾液化反应中观察到极好的结果和完全的立体选择性,但结果受溶剂和/或糖基受体性质的影响。
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
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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