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

  • Huang Jing ,
  • Yang Yihua ,
  • Feng Juan ,
  • Li Junzhang ,
  • Liu Shouxin
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  • 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 date: 2019-11-25

  Revised date: 2020-01-15

  Online 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).

Abstract

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.

Cite this article

Huang Jing , Yang Yihua , Feng Juan , Li Junzhang , Liu Shouxin . Research Progress on cis-/trans-Isomerization of Cyclic Peptide[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1473 -1483 . DOI: 10.6023/cjoc201911030

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