Traceless ligation of cysteine peptides using selective deselenization

Norman Metanis; Ehud Keinan; Philip E. Dawson

doi:10.1002/anie.201001900

Traceless ligation of cysteine peptides using selective deselenization

Norman Metanis^*, Ehud Keinan, Philip E. Dawson

^*Corresponding author for this work

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

168 Scopus citations

Abstract

Selective deselenization: Native chemical ligation at selenocysteine is followed by selective deselenization of the selenocysteine to alanine, in the presence of cysteine residues without protecting groups (see scheme). This selectivity is achieved by using the water-soluble tris(2-carboxyethyl)phosphine (TCEP) in the absence of a radical initiator.

Original language	English
Pages (from-to)	7049-7053
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	39
DOIs	https://doi.org/10.1002/anie.201001900
State	Published - 17 Sep 2010
Externally published	Yes

Keywords

Deselenization
Desulfurization
Native chemical ligation
Peptides
Protein modification

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10.1002/anie.201001900

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AU - Metanis, Norman

AU - Keinan, Ehud

AU - Dawson, Philip E.

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N2 - Selective deselenization: Native chemical ligation at selenocysteine is followed by selective deselenization of the selenocysteine to alanine, in the presence of cysteine residues without protecting groups (see scheme). This selectivity is achieved by using the water-soluble tris(2-carboxyethyl)phosphine (TCEP) in the absence of a radical initiator.

AB - Selective deselenization: Native chemical ligation at selenocysteine is followed by selective deselenization of the selenocysteine to alanine, in the presence of cysteine residues without protecting groups (see scheme). This selectivity is achieved by using the water-soluble tris(2-carboxyethyl)phosphine (TCEP) in the absence of a radical initiator.

KW - Deselenization

KW - Desulfurization

KW - Native chemical ligation

KW - Peptides

KW - Protein modification

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JF - Angewandte Chemie - International Edition

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ER -

Traceless ligation of cysteine peptides using selective deselenization

Abstract

Keywords

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