Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction

Julien Tailhades; Marie Aude Gidel; Benjamin Grossi; Jennifer Lécaillon; Luc Brunel; Gilles Subra; Jean Martinez; Muriel Amblard

doi:10.1002/anie.200904276

Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction

Julien Tailhades, Marie Aude Gidel, Benjamin Grossi, Jennifer Lécaillon, Luc Brunel, Gilles Subra, Jean Martinez, Muriel Amblard

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

35 Citations (Scopus)

Abstract

Getting the better of troublemakers: C-terminal peptide alcohols cannot be synthesized by conventional solidphase peptide synthesis (SPPS) because of the absence of a free carboxylic group to attach to the resin. This problem was circumvented by anchoring a β-amino alcohol residue to the resin to provide a starting point for SPPS. An intramolecular O-N acyl shift completed the synthesis of the desired peptides (see scheme).

Original language	English
Pages (from-to)	117-120
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	1
DOIs	https://doi.org/10.1002/anie.200904276
Publication status	Published - 4 Jan 2010
Externally published	Yes

Keywords

Isopeptides
Mitsunobu reaction
O-n acyl shift
Peptide alcohols
Solid-phase synthesis

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10.1002/anie.200904276

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AU - Gidel, Marie Aude

AU - Grossi, Benjamin

AU - Lécaillon, Jennifer

AU - Brunel, Luc

AU - Subra, Gilles

AU - Martinez, Jean

AU - Amblard, Muriel

PY - 2010/1/4

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KW - Isopeptides

KW - Mitsunobu reaction

KW - O-n acyl shift

KW - Peptide alcohols

KW - Solid-phase synthesis

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Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction

Abstract

Keywords

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