Synlett 2017; 28(15): 1966-1970
DOI: 10.1055/s-0036-1588870
cluster
© Georg Thieme Verlag Stuttgart · New York

Aspartic Acid Side-Chain Benzyl Ester as a Multifunctionalization Precursor for Synthesis of Branched and Cyclic Arginylglycylaspartic Acid Peptides

Xiaobo Tian
a  CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, P. R. of China
b  Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, P. R. of China
,
Pengqiu Yu
a  CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, P. R. of China
b  Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, P. R. of China
,
Yubo Tang
a  CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, P. R. of China
,
Zhiping Le*
b  Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, P. R. of China
,
Wei Huang*
a  CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, P. R. of China
c  University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, P. R. of China   Email: huangwei@simm.ac.cn   Email: zple@ncu.edu.cn
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (NNSFC, No. 21372238 and 21572244) and the Personalized Medicines: Molecular Signature-Based Drug Discovery and Development Strategic Priority Research Program of the Chinese Academy of Sciences, Grant No. XDA12020311.
Further Information

Publication History

Received: 16 April 2017

Accepted after revision: 16 May 2017

Publication Date:
29 June 2017 (online)


These authors contributed equally to this work.

Published as part of the Cluster Recent Advances in Protein and Peptide Synthesis

Abstract

Here, we report a peptide aspartic acid side-chain benzyl ester as a useful precursor that can be efficiently converted into various functional groups, including acid, amide, carbonyl hydrazide, carbonyl azide, or thio ester groups, without other protection for the peptide. With this strategy, we synthesized a series of novel branched and cyclic arginylglycylaspartic acid peptides through successive peptide C-terminal ligation and side-chain ligation based on a side-chain carbonyl azide or thio ester.

Supporting Information

 
  • Notes and References

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