研究亮点

通过基于多肽酰肼的化学连接反应合成高张力环状四肽

  • 刘(氵凾) ,
  • 李学臣
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  • 香港大学化学系

收稿日期: 2014-11-27

  网络出版日期: 2014-12-01

Synthesis of Highly-strained Cyclic Tetrapeptides via Peptide Hydrazide Based Ligation

  • Liu Han ,
  • Li Xuechen
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  • Department of Chemistry, The University of Hong Kong

Received date: 2014-11-27

  Online published: 2014-12-01

摘要

刘磊课题组采用其发展的基于多肽酰肼的化学连接反应, 成功合成了一系列高张力环状四肽分子. 多肽酰肼在温和氧化条件下活化为多肽酰基叠氮中间体, 随后与4-巯基苯乙酸形成硫酯, 进而经由分子内天然化学连接反应得到环状四肽. 通过后续的自由基脱硫反应, 可得到连接位点为丙氨酸的产物.

本文引用格式

刘(氵凾) , 李学臣 . 通过基于多肽酰肼的化学连接反应合成高张力环状四肽[J]. 化学学报, 2014 , 72(12) : 1197 -1198 . DOI: 10.6023/A14110820

Abstract

A series of highly-strained cyclic tetrapeptides were efficiently synthesized via peptide hydrazide based ligation, reported by Liu et al. Upon mild oxidative activation, the peptide hydrazide was transformed into a highly active peptide azide intermediate and then in situ converted into a peptide 4-mercaptophenylacetic acid (MPAA) thiol ester, which underwent native chemical ligation (NCL)-mediated cyclization to afford the desired cyclic tetrapeptides. After radical desulfurization, the product with alanine residue at the ligation site can be obtained.

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