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

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

Jian Lu ^a ,
Xiao-Bo Tian ^a,b ,
Wei Huang ^a,,

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: 14 April 2015
Fund Project: This work was supported by the National Natural Science Foundation of China (NNSFC, No. 21372238) (NNSFC, No. 21372238)

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.
- Branched cyclic peptide,
- Asn side-chain ligation,
- Hydrazide ligation,
- Neopeptide
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