有机化学 ›› 2019, Vol. 39 ›› Issue (9): 2379-2391.DOI: 10.6023/cjoc201903038 上一篇    下一篇

综述与进展

点击反应在糖聚肽及其类似物合成中的应用

王昭a,c, 郝凌云a, 张小娟a, 盛瑞隆b,c   

  1. a 金陵科技学院材料工程学院 南京市视光材料与技术重点实验室 南京 211169;
    b CQM-Centro de Química da Madeira, Universidade da Madeira, Campus da Penteada, Funchal, 9000-390 Portugal;
    c 中国科学院上海有机化学研究所 上海 200032
  • 收稿日期:2019-03-21 修回日期:2019-04-19 出版日期:2019-09-25 发布日期:2019-05-06
  • 通讯作者: 盛瑞隆 E-mail:ruilong.sheng@staff.uma.pt
  • 基金资助:

    国家自然科学基金(No.21372251)、金陵科技学院高层次人才科研启动基金(No.jit-b-201828)、葡萄牙科学技术基金(No.PEst-OE/QUI/UI0674/2019)、科学仪器和基础设备专项基金(No.M1420-01-0145-FEDER-000008)、区域研究技术创新基金(No.M1420-01-0145-FEDER-000005)子课题2017-ISG-003资助项目.

Advances of “Click” Reaction Approach in Glycopolypeptide Synthesis

Wang Zhaoa,c, Hao Lingyuna, Zhang Xiaojuana, Sheng Ruilongb,c   

  1. a School of Material Engineering, Jinling Institute of Technology, Nanjing 211169, China;
    b CQM-Centro de Química da Madeira, Universidade da Madeira, Campus da Penteada, 9000-390 Funchal, Portugal;
    c Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  • Received:2019-03-21 Revised:2019-04-19 Online:2019-09-25 Published:2019-05-06
  • Contact: 10.6023/cjoc201903038 E-mail:ruilong.sheng@staff.uma.pt
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372251), the Research Initiation Fund for High-level Talents of Jinling University of Science and Technology (No. jit-b-201828), the Fundação para a Ciência e a Tecnologia (No. PEst-OE/QUI/UI0674/2019), the Reforço do Investimento em Equipamentos e Infraestruturas Científicas na RAM (No. M1420-01-0145-FEDER-000008), and the Sub Topic 2017-ISG-003 of Agência Regional para o Desenvolvimento da Investigação Tecnologia e Inovação (No. M1420-01-0145-FEDER-000005).

糖聚肽是一类由聚肽/聚氨基酸与糖类化合物共价相连构成的高分子化合物,因其良好的生物相容性及独特的生物学性能,在自组装、组织工程、药物输送等领域均显示出广泛的应用前景,成为近年来蓬勃发展的热点领域.高效合成结构规整可控的糖聚肽是该领域的热点和难点.点击化学的快速发展为糖聚肽的合成提供了高效便捷的途径.系统综述了点击反应在糖聚肽两种合成策略中的应用——通过聚合后修饰法将糖分子引入到聚氨基酸前体侧链上以及对糖苷化的α-氨基酸-N-羧酸酐(glyco-NCA)"可点击"化学单体的开环聚合反应,同时也总结了通过点击反应将含糖功能基元化学偶联到聚氨基酸链末端合成糖聚肽类似物的策略,并对其优缺点和发展方向进行了简要讨论.

关键词: 糖聚肽, 点击反应, 聚合后修饰, 开环聚合

Synthetic glycopolypeptides, as analogues of natural glycoproteins, are an emerging class of bioinspired polymers with excellent biocompatibility. They can mimic the structure and functions of natural glycoproteins, and show great potential for biological applications, such as biomolecular recognition, drug/gene delivery, cell adhesion and targeting, as well as cell culture and tissue engineering. Nevertheless, the efficient and lab/pilot scale preparation of well-defined and tunable glycopolypeptides with complex polymer structures, has been a challenging field until now. The fast development of "Click" chemistry/reaction offers versatile and powerful tools for the synthesis of glycopolypeptides. The state of arts for the development of new "Click" synthetic strategies and methods in the preparation of glycopolypeptides, mainly including post-polymerization glycosylation of synthetic polypeptides and ring-opening polymerization of glycosylated N-carboxyanhydride (glyco-NCA) is reviewed. The pros and cons of current developments for the synthesis of glycopolypeptide analogues and their future perspectives are also stated and discussed.

Key words: glycopolypeptide, “Click&rdquo, reaction, post-polymerization glycosylation, ring-opening polymerization