One-Pot Glycosylation (OPG) for the Chemical Synthesis of Oligosaccharides
One-Pot Glycosylation (OPG) for the Chemical Synthesis of Oligosaccharides
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DOI：
10.2174/1385272053369240
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发表时间：
2005
影响因子：
2.6
通讯作者：
Biao Yu;Zunyi Yang;Hongzhi Cao
中科院分区：
文献类型：
--
作者：
Biao Yu;Zunyi Yang;Hongzhi Cao
从1993年Kahne和Raghavan首次报道到2003年5月，综述了化学合成低聚糖的“一锅糖基化”策略。OPG的实质是区分一对糖基化供体或受体的反应性差异，从而在不纯化第一步偶联产物的情况下，依次进行两个糖基化步骤。因此，根据引起反应性差异的主要立体电子因素对文献报道进行分组，包括“武装-解除武装效应”、“离去基团正交性”、“可区分受体”和“杂化”。“杂交”OPG工艺利用了一组武装-解除武装的给体、正交离去基和受体的反应性差异的结合，在一个锅中依次进行三个或多个糖基化步骤。在低聚糖合成过程中，给体和受体反应性差异的相关概念和利用，最终演变为OPG或平行推进，本文在开始部分作了简要介绍。
This review provides a comprehensive survey of the "one pot glycosylation" (OPG) strategy for the chemical synthesis of oligosacchari des, covering literatures from the first example reported by Kahne and Raghavan in 1993 through May 2003. The essence of the OPG is to distinguish the reactivity difference of a pair of the glycosylation donors or acceptors so as to carry out two glycosylation steps sequentially without purification of the first-step coupling product. Accordingly, the literature reports are grouped based on the major stereoelectronic factors causing the reactivity differences, those include the "armed-disarmed effect", "orthogonality of leaving groups", "distinguishable acceptors", and "the hybrid". "The hybrid" OPG procedure takes advantage of a combination of the reactivity disparity of a set of the armed-disarmed donors, orthogonal leaving groups, as well as acceptors so as to proceed three or more steps of glycosylation sequentially in one pot. Relevant conception and exploitation of the reactivity differences of the donors and acceptors in the synthesis of oligosaccharides, which finally evolve the OPG or advance parallelly, are briefly described at the beginning.