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Polymer‐bound alkyltriazenes for mild racemization‐free esterification of amino acid and peptide derivatives
Author(s) -
Smerdka Joachim,
Rademann Jörg,
Jung Günther
Publication year - 2004
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.581
Subject(s) - racemization , chemistry , alkylation , amino acid , peptidomimetic , moiety , peptide , alkyl , peptide synthesis , organic chemistry , carboxylate , combinatorial chemistry , catalysis , biochemistry
A novel tool for polymer‐assisted solution phase (PASP) esterification of amino acid and peptide derivatives has been developed. When treated with carboxylic acids, polymer‐bound alkyltriazenes react with a loss of nitrogen and transfer of the alkyl moiety to the carboxylate anion to form the corresponding alkyl esters. There are no limitations with regard to either the protecting groups or the nature of the amino acid. Furthermore no racemization occurs at the chiral centers of the amino acids as demonstrated by chiral GC‐MS analyses. Alkyltriazene‐resins were also applied successfully to the esterification of peptide acids and other peptidic structures, such as tripalmitoyl‐ S ‐glyceryl‐cysteine (Pam 3 Cys). The triazene‐mediated esterification reaction is exceptionally mild, and there is no need for prior activation of the carboxy groups. This method is therefore particularly suitable for the alkylation of complex peptidomimetic structures prone to racemization and for acid‐sensitive structures. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.