Document Detail

An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride.
MedLine Citation:
PMID:  20112295     Owner:  NLM     Status:  MEDLINE    
Dehydroamino acids are important precursors for the synthesis of a number of unnatural amino acids and are structural components in many biologically active peptide derivatives. However, efficient synthetic procedures for their production in large amounts and without side reactions are limited. We report here an improved procedure for the synthesis of dehydroalanine and dehydroamino butyric acid from the carbonate derivatives of serine and threonine using TBAF. The antiselective E(2) elimination of the carbonate derivatives of serine and threonine using TBAF is milder and more efficient than other available procedures. The elimination reaction is completed in less than 10 min with various carbonate derivatives studied and the methodology is very efficient for the synthesis of dehydroamino acids and dehydropeptides. The procedure thus provides an easy access to key synthetic precursors and can be used to introduce interesting structural elements to designed peptides.
Ramesh Ramapanicker; Roli Mishra; Srinivasan Chandrasekaran
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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:  16     ISSN:  1099-1387     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2010 Mar 
Date Detail:
Created Date:  2010-02-15     Completed Date:  2010-05-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  123-5     Citation Subset:  IM    
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
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MeSH Terms
Alanine / analogs & derivatives*,  chemical synthesis,  chemistry
Carbonates / chemistry
Peptides / chemical synthesis*,  chemistry
Quaternary Ammonium Compounds / chemistry*
Serine / chemistry*
Threonine / chemistry*
gamma-Aminobutyric Acid / analogs & derivatives*,  chemical synthesis,  chemistry
Reg. No./Substance:
0/Carbonates; 0/Peptides; 0/Quaternary Ammonium Compounds; 10549-76-5/tetrabutylammonium; 1948-56-7/dehydroalanine; 56-12-2/gamma-Aminobutyric Acid; 56-41-7/Alanine; 56-45-1/Serine; 71018-10-5/alpha, beta-dehydroaminobutyric acid; 72-19-5/Threonine

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