Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2379-2391.DOI: 10.6023/cjoc201903038 Previous Articles     Next Articles

REVIEW

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).

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