Facile peptide thioester synthesis via solution-phase tosylamide preparation

Shino Manabe; Tomoyuki Sugioka; Yukishige Ito

doi:10.1016/j.tetlet.2006.11.143

Facile peptide thioester synthesis via solution-phase tosylamide preparation

Shino Manabe, Tomoyuki Sugioka, Yukishige Ito

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

16 Citations (Scopus)

Abstract

Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation.

Original language	English
Pages (from-to)	849-853
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2006.11.143
Publication status	Published - 2007 Jan 29
Externally published	Yes

Keywords

Glycopeptide
Sequential peptide ligation
Thioester

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.11.143

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abstract = "Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation.",

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AU - Manabe, Shino

AU - Sugioka, Tomoyuki

AU - Ito, Yukishige

PY - 2007/1/29

Y1 - 2007/1/29

N2 - Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation.

AB - Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation.

KW - Glycopeptide

KW - Sequential peptide ligation

KW - Thioester

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JF - Tetrahedron Letters

IS - 5

ER -

Facile peptide thioester synthesis via solution-phase tosylamide preparation

Abstract

Keywords

ASJC Scopus subject areas

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