C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

Jonas Hansen; Frederik Diness; Morten Peter Meldal

doi:10.1039/c6ob00213g

C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

Jonas Hansen, Frederik Diness, Morten Peter Meldal

Department of Chemistry

19 Citations (Scopus)

72 Downloads (Pure)

Abstract

A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.

Original language	English
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	12
Pages (from-to)	3238-3245
Number of pages	8
ISSN	1477-0520
DOIs	https://doi.org/10.1039/c6ob00213g
Publication status	Published - 2016

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10.1039/c6ob00213gLicence: CC BY

C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophilesFinal published version, 297 KBLicence: CC BY

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abstract = "A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.",

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AU - Diness, Frederik

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AB - A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.

U2 - 10.1039/c6ob00213g

DO - 10.1039/c6ob00213g

M3 - Journal article

C2 - 26924021

SN - 1470-4358

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 12

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C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

Abstract

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