Document Detail

Polymer-bound alkyltriazenes for mild racemization-free esterification of amino acid and peptide derivatives.
MedLine Citation:
PMID:  15526709     Owner:  NLM     Status:  MEDLINE    
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 (Pam3Cys). 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.
Joachim Smerdka; Jörg Rademann; Günther Jung
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of peptide science : an official publication of the European Peptide Society     Volume:  10     ISSN:  1075-2617     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2004 Oct 
Date Detail:
Created Date:  2004-11-05     Completed Date:  2005-04-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  603-11     Citation Subset:  IM    
Institute of Organic Chemistry, University of Tübingen, 72076 Tübingen, Germany.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Combinatorial Chemistry Techniques*
Peptides / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Amino Acids; 0/Peptides; 0/Polymers; 0/Triazenes

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