有机化学 ›› 2020, Vol. 40 ›› Issue (6): 1473-1483.DOI: 10.6023/cjoc201911030 上一篇    下一篇

综述与进展

环肽中酰胺键cis-/trans-异构化的相关研究进展

黄净a, 杨毅华b, 冯娟b, 李军章b, 刘守信a   

  1. a 河北科技大学 省部共建国家重点实验室培育基地-河北省药用分子化学重点实验室 河北石家庄 050018;
    b 河北科技大学化学与制药工程学院 河北石家庄 050018
  • 收稿日期:2019-11-25 修回日期:2020-01-15 发布日期:2020-03-11
  • 通讯作者: 杨毅华, 刘守信 E-mail:yihuayang@hebust.edu.cn;chlsx@hebust.edu.cn
  • 基金资助:
    “973”计划前期研究专项课题(Nos.2011CB512007,2012CB723501)和国家自然科学基金(Nos.30472074,30873139)资助项目.

Research Progress on cis-/trans-Isomerization of Cyclic Peptide

Huang Jinga, Yang Yihuab, Feng Juanb, Li Junzhangb, Liu Shouxina   

  1. a State Key Laboratory Breeding Base, Hebei Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science & Technology, Shijiazhuang, Hebei 050018;
    b College of Chemical and Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang, Hebei 050018
  • Received:2019-11-25 Revised:2020-01-15 Published:2020-03-11
  • Supported by:
    Project supported by the National Basic Research Program of China (Nos. 2011CB512007, 2012CB723501), and the National Natural Science Foundation of China (Nos. 30472074, 30873139).

介绍了环肽化合物中顺式(cis-)和反式(trans-)结构特点,分别针对不含N-取代的环肽、含脯氨酸残基的环肽以及含N-甲基化残基的天然环肽,讨论了cis-或trans-结构在上述环肽及结构类似物中的研究进展,以及这种cis-或trans-结构对环肽生物活性的潜在影响.脯氨酸由于其刚性吡咯环结构而显著影响着环肽分子构象,N-甲基化残基不仅增大了空间位阻,而且能够诱导增大酰胺键cis-结构比例.

关键词: cis-/trans-结构, cis-/trans-异构体, 环肽, 生物活性

This paper focuses on cis-/trans-conformational interchanges of amide bonds in cyclic peptides that contain N-unsubstituted amino acids, N-methylated amino acids, and prolines. Conformational preferences of such cyclic peptides and their analogs are discussed. Proline has strong influences on the conformation due to the five-membered cyclic structure. N-Methylation not only increased the steric hindrance, but also led to increased population of cis-conformation of the amide bond.

Key words: cis-/trans-structure, cis-/trans-isomerization, cyclic peptide, bioactivity