An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride

Ramapanicker, Ramesh and Mishra, Roli and Chandrasekaran, Srinivasan (2010) An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride. In: Journal of Peptide Science, 16 (3). pp. 123-125.

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Abstract

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. Copyright

Item Type:	Journal Article
Publication:	Journal of Peptide Science
Publisher:	John Wiley and Sons.
Additional Information:	Copyright of this article belongs to John Wiley and Sons.
Keywords:	amino acids; peptides; elimination; carbonates
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	30 Mar 2010 10:02
Last Modified:	19 Sep 2010 05:58
URI:	http://eprints.iisc.ac.in/id/eprint/26639

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