化学学报 ›› 2019, Vol. 77 ›› Issue (7): 581-597.DOI: 10.6023/A19040128 上一篇    下一篇

综述

多糖化学合成研究进展

吴勇, 叶新山   

  1. 天然药物及仿生药物国家重点实验室 北京大学药学院 北京 100191
  • 收稿日期:2019-04-11 出版日期:2019-07-15 发布日期:2019-06-06
  • 通讯作者: 叶新山 E-mail:xinshan@bjmu.edu.cn
  • 作者简介:吴勇,博士,1990年出生于四川资阳,2013年在四川大学华西药学院获得学士学位,随后加入北京大学天然药物及仿生药物国家重点实验室叶新山教授课题组,并于2018年获得博士学位.博士阶段主要研究具有重要生物活性复杂多糖的化学合成;叶新山,博士,教授,分别于1985和1988年在武汉大学获得学士和硕士学位,1996年在香港中文大学获得博士学位,之后在美国斯克利普斯研究所从事博士后研究.2000年回国后加入北京大学药学院,主要研究兴趣包括新的聚糖化学合成方法和策略的发展、生物活性聚糖(包括肿瘤相关糖抗原)的合成和活性评价以及基于糖类的新药的发现.
  • 基金资助:

    项目受国家自然科学基金重点项目(No.21738001)资助.

Recent Advances in Chemical Synthesis of Polysaccharides

Wu Yong, Ye Xin-Shan   

  1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191
  • Received:2019-04-11 Online:2019-07-15 Published:2019-06-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21738001).

多糖是一类结构复杂的生物大分子,广泛分布于微生物、植物、动物等生物体中,参与众多重要的生命过程.然而,多糖研究一直受限于难以获得足量结构均一的多糖物质,这使得多糖的结构和功能研究及其相关的应用研究进展缓慢.近几十年来,随着糖合成技术的进步,糖的化学合成效率不断提高,人们开始关注复杂多糖的化学合成,并取得了一些进展.本文主要对多糖化学合成所涉及的糖基化方法、糖组装策略和代表性的合成工作进行综述,并对研究前景进行展望.

关键词: 多糖, 化学合成, 糖基化方法, 合成策略

Polysaccharides are a class of bio-macromolecules with highly complex structures that are widely found in living organisms such as microorganisms, plants and animals. Polysaccharides serve not only as structural components and energy sources of cells, but also as important signaling molecules which are involved in many key biological processes. Studies on polysaccharide-mediated biological processes require access to structurally defined molecules, which approach the size and complexity of those found in nature, but naturally-occurring polysaccharides usually exist in microheterogeneous forms, making it difficult or even impossible to isolate pure polysaccharides from natural sources in most cases. Chemical synthesis represents a reliable solution to this problem, which can provide polysaccharide samples with defined chemical structures for functional studies and even a library of analogs of natural glycans for structure-activity relationship investigations. But unlike oligonucleotides and peptides, which can already be obtained by automated synthesizers in a very short of time, the chemical synthesis of glycans remains a great challenge for synthetic chemists. The major challenge for glycan synthesis lies in the need to handle both stereo-and regio-chemistry in the construction of each glycosyl linkage, and the extensive protecting-group manipulations as well as much intermediate separation make it a tedious and time-consuming process. Over the past decades, carbohydrate chemists have developed many glycosylation reactions. A series of strategies for glycan assembly have been also established. The advances in both synthetic methods and strategies have significantly increased the synthetic efficiency of carbohydrate molecules, and many great accomplishments in the field of polysaccharide synthesis have been witnessed in recent decades. Some representative methods and strategies, and their successful applications in the chemical synthesis of complex polysaccharides are summarized in this review.

Key words: polysaccharide, chemical synthesis, glycosylation method, synthetic strategy