A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation

注册 English

A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation

Jian Lu , Xiao-Bo Tian , Wei Huang

Citation: Jian Lu, Xiao-Bo Tian, Wei Huang. A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation[J]. Chinese Chemical Letters, 2015, 26(8): 946-950. doi: 10.1016/j.cclet.2015.05.016 shu

shu

A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation

通讯作者: Wei Huang,

基金项目:
This work was supported by the National Natural Science Foundation of China (NNSFC, No. 21372238) (NNSFC, No. 21372238)

Shanghai Pujiang Talent Program (No. 13PJ1410200). We thank the members in Huang's group for helpful discussion (No. 13PJ1410200)

摘要: Here, we report a new strategy for rapid synthesis of branched peptide by side-chain hydrazide ligation at Asn. The hydrazide was converted to thioester at Asn side chain by NaNO₂ and thiol reagent, and sequential ligation with an N-terminus Cys-peptide efficiently afforded the branched peptide. A branched cyclic peptide was successfully synthesized by side-chain ligation with a two-Cys-peptide and formation of a disulfide bond. This approach provides a new way for expeditious synthesis of branched peptides and facilitates the design of neopeptides as functional bio-mimics.

关键词:

English

A new strategy for synthesis of branched cyclic peptide by Asn side-chain hydrazide ligation

1.
a CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;
2.
b Medical College of Nanchang University, Nanchang 330006, China

Corresponding author: Wei Huang,

Received Date: 30 March 2015
Available Online: 15 May 2015
Fund Project:

Abstract: Here, we report a new strategy for rapid synthesis of branched peptide by side-chain hydrazide ligation at Asn. The hydrazide was converted to thioester at Asn side chain by NaNO₂ and thiol reagent, and sequential ligation with an N-terminus Cys-peptide efficiently afforded the branched peptide. A branched cyclic peptide was successfully synthesized by side-chain ligation with a two-Cys-peptide and formation of a disulfide bond. This approach provides a new way for expeditious synthesis of branched peptides and facilitates the design of neopeptides as functional bio-mimics.

Key words:

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