Direct on-resin synthesis of peptide-αthiophenylesters for use in native chemical ligation

Duhee Bang; Brad L. Pentelute; Zachary P. Gates; Stephen B. Kent

doi:10.1021/ol052811j

Direct on-resin synthesis of peptide-^αthiophenylesters for use in native chemical ligation

Duhee Bang, Brad L. Pentelute, Zachary P. Gates, Stephen B. Kent

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

A peptide-^αthiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-^αthiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-^αthiophenylesters using a simple and efficient method. The peptide- ^αthiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-^αthioalkylester.

Original language	English
Pages (from-to)	1049-1052
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	6
DOIs	https://doi.org/10.1021/ol052811j
Publication status	Published - 2006 Mar 16

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol052811j

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abstract = "A peptide-αthiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-αthiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-αthiophenylesters using a simple and efficient method. The peptide- αthiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-αthioalkylester.",

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AU - Bang, Duhee

AU - Pentelute, Brad L.

AU - Gates, Zachary P.

AU - Kent, Stephen B.

PY - 2006/3/16

Y1 - 2006/3/16

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AB - A peptide-αthiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-αthiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-αthiophenylesters using a simple and efficient method. The peptide- αthiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-αthioalkylester.

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Direct on-resin synthesis of peptide-^αthiophenylesters for use in native chemical ligation

Abstract

All Science Journal Classification (ASJC) codes

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