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2022 , Vol. 42 >Issue 11: 3506 - 3529

DOI: https://doi.org/10.6023/cjoc202204050

综述与进展

官能团导向立体选择性的糖苷化反应研究进展

  • 孙阳星 ,
  • 李彦芝 ,
  • 曹燕来 ,
  • 王能中 ,
  • 向少华 ,
  • 刘明国 ,
  • 姚辉
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  • a三峡大学生物与制药学院 中国轻工业功能酵母重点实验室 天然产物研究与利用湖北省重点实验室 湖北宜昌 443002
    b湖北广辰药业有限公司 湖北宜昌 443002
    c南方科技大学 深圳格拉布斯研究院化学系 广东省催化重点实验室 广东深圳 518055

收稿日期: 2022-04-19

  修回日期: 2022-07-06

  网络出版日期: 2022-08-18

基金资助

高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2020CFB205); 深圳市科创委基础研究自由探索(JCYJ20180305123508258)

收起

Research Advances in Functional Group-Directed Stereoselective Glycosylation

  • Yangxing Sun ,
  • Yanzhi Li ,
  • Yanlai Cao ,
  • Nengzhong Wang ,
  • Shaohua Xiang ,
  • Mingguo Liu ,
  • Hui Yao
Expand
  • aKey Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002
    bHubei Guangchen Pharmaceutical Co. Ltd, Yichang, Hubei 443002
    cGuangdong Provincial Key Laboratory of Catalysis, Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055
*E-mail: ;

Received date: 2022-04-19

  Revised date: 2022-07-06

  Online published: 2022-08-18

Supported by

Programme of Introducing Talents of Discipline to Universities (111 Project)(D20015); Natural Science Foundation of Hubei Province(2020CFB205); Shenzhen Special Funds(JCYJ20180305123508258)

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摘要

糖类化合物不仅是生命活动的能量来源, 还在许多细胞信号传导和药物研发中发挥着至关重要的作用. 糖化学的核心是糖苷化反应, 而开发一种通用、高效的立体选择性糖苷化方法仍是一大挑战. 目前主要从糖供体、催化条件以及糖受体三个方面进行立体选择性糖苷化反应研究, 其中研究最多的是糖供体的开发. 主要综述了近十年来糖供体的官能团对糖苷化立体选择性调控的发展, 根据官能团参与糖苷化反应的方式可将其分为五大类: 邻基参与型官能团、远程参与型官能团、分子内苷元传递型官能团、与催化剂配位型官能团及氢键作用型官能团.

关键词： 糖类化合物; 糖苷化反应; 官能团; 立体选择性合成

本文引用格式

孙阳星 , 李彦芝 , 曹燕来 , 王能中 , 向少华 , 刘明国 , 姚辉 . 官能团导向立体选择性的糖苷化反应研究进展[J]. 有机化学, 2022 , 42(11) : 3506 -3529 . DOI: 10.6023/cjoc202204050

Abstract

Carbohydrates are not only an energy source for life activities, but also play a vital role in many physiological activities and drug development. Glycosylation is the core reaction of carbohydrate chemistry, and it is still a big challenge to develop a general stereoselective and efficent glycosylation method. The control of stereoselectivity is mainly carried out from three aspects: glycosyl donors, catalytic conditions and glycosyl acceptors. Among them, the development of glycosyl donors is the most concerned. The development of functional group of glycosyl donors on stereoselective regulation in the past decades is summarized. According to the way in which the functional groups participate in the glycosylation reactions, they are divided into neighboring-group participating groups, remote group participating groups, intramolecular aglycone delivery groups, coordination functional groups and hydrogen-bonding mediated groups.

Key words： carbohydrate; glycosylation reaction; functional group; stereoselective synthesis

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