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Synthesis of Peptide Alcohols on the Basis of an O–N Acyl‐Transfer Reaction
Author(s) -
Tailhades Julien,
Gidel MarieAude,
Grossi Benjamin,
Lécaillon Jennifer,
Brunel Luc,
Subra Gilles,
Martinez Jean,
Amblard Muriel
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200904276
Subject(s) - intramolecular force , peptide , peptide synthesis , chemistry , combinatorial chemistry , alcohol , residue (chemistry) , computer science , organic chemistry , stereochemistry , biochemistry
Getting the better of troublemakers : C‐terminal peptide alcohols cannot be synthesized by conventional solid‐phase 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).