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2014 , Vol. 34 >Issue 3: 450 - 460

DOI: https://doi.org/10.6023/cjoc201311001

综述与进展

骨架环肽的化学合成研究进展

  • 司岩岩 ,
  • 郭叶 ,
  • 李海燕 ,
  • 孙浩源 ,
  • 方葛敏
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  • a 中国科学院合肥物质研究院强磁场科学中心 合肥 230031;
    b 清华大学化学系 北京 100084;
    c 辽宁大学生命科学院 沈阳 110036

收稿日期: 2013-11-01

  修回日期: 2013-11-19

  网络出版日期: 2013-12-06

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Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

  • Si Yanyan ,
  • Guo Ye ,
  • Li Haiyan ,
  • Sun Haoyuan ,
  • Fang Gemin
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  • a High Magnetic Field Laboratory, Chinese Academy of Sciences, Hefei 230031;
    b Department of Chemistry, Tsinghua University, Beijing 100084;
    c College of Life Science, Liaoning University, Shenyang 110036

Received date: 2013-11-01

  Revised date: 2013-11-19

  Online published: 2013-12-06

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摘要

骨架环肽是线性肽的C端和N端通过酰胺键进行首尾环合而形成的环状分子. 研究者从细菌、真菌、植物和动物中发现了大量的骨架环肽. 这种首尾环合的结构，使得骨架环肽具有很好的酶稳定性、热稳定性和化学稳定性，部分骨架环肽具有细胞膜通透性. 骨架环肽分子异常的稳定性和高效的生物活性，使得其成为目前药物领域的研究热点. 为了更深入地研究它们的结构和功能，骨架环肽的制备成为一个重要问题. 概述了化学合成骨架环肽的一些方法，包括：（1）固相环合策略；（2）液相环合策略；（3）分子内自然化学连接策略，并对这些方法的特点和效率进行了讨论比较.

关键词： 骨架环肽; 环化; 自然化学连接

本文引用格式

司岩岩 , 郭叶 , 李海燕 , 孙浩源 , 方葛敏 . 骨架环肽的化学合成研究进展[J]. 有机化学, 2014 , 34(3) : 450 -460 . DOI: 10.6023/cjoc201311001

Abstract

Backbone cyclized peptides belong to a family of circular polypeptide molecules in which the carboxyl and amino termini are covalently linked by an amide bond. Over the last almost 20 years, the backbone cyclized peptides have been discovered in bacteria, fungi, plants and animals. Compared with their linear precursors, the backbone cyclized peptides have a head-to-tail cyclic backbone enabling them to resist enzymatic degradation and to improve their thermal and chemical stability. Remarkably, some of them even have cell membrane permeability. Due to their exceptionally intracellular stability and potent bioactivities, backbone cyclized peptide is emerging as one of the most interesting molecules in the area of drug discovery. To study the structure and function of backbone cyclized peptides in detail, it is necessary to develop efficient approaches for the synthesis of these molecules. Herein, the recent advances in chemical synthesis of backbone cyclized peptides with respect to cyclization strategies are reviewed, including solid phase-based cyclization, liquid-phase cyclization, and intramolecular native chemical ligation.

Key words： backbone cyclized peptides; chemical synthesis; native chemical ligation

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