Synthesis of Branched Peptides via a Side-Chain Benzyl Ester

Junjie Liu; Jian Li; Xiaobo Tian; Feng Tang; Wei Huang

doi:10.1007/978-1-0716-0227-0_12

Synthesis of Branched Peptides via a Side-Chain Benzyl Ester

Methods Mol Biol. 2020:2103:189-198. doi: 10.1007/978-1-0716-0227-0_12.

Authors

Junjie Liu^{1

2}, Jian Li^{1

3}, Xiaobo Tian¹, Feng Tang^{1

3}, Wei Huang^{4

5}

Affiliations

¹ CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China.
² Department of Chemistry, Nanchang University, Nanchang, P. R. China.
³ University of Chinese Academy of Sciences, Beijing, China.
⁴ CAS Key Laboratory of Receptor Research, CAS Center for Excellence in Molecular Cell Science, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China. huangwei@simm.ac.cn.
⁵ University of Chinese Academy of Sciences, Beijing, China. huangwei@simm.ac.cn.

PMID: 31879926
DOI: 10.1007/978-1-0716-0227-0_12

Abstract

Branched peptide as an attractive mimic of natural peptide is widely used in structural design of functional or therapeutic peptides, to improve their biological activity, stability, and pharmacokinetic properties. In this protocol, we employ a function group of side-chain benzyl ester as the precursor of hydrazide, which could be conveniently used to assemble a branch peptide by native chemical ligation or direct amidation. This method is convergent and efficient, and facilitates the synthesis and application of branched peptides.

Keywords: Amidation; Branched peptide; Hydrazinolysis; Native chemical ligation; Side-chain benzyl ester.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chemistry Techniques, Synthetic*
Chromatography, High Pressure Liquid
Esters / chemistry*
Peptides / analysis
Peptides / chemical synthesis*
Peptides / chemistry

Substances

Esters
Peptides