"Customizable" units in Di- and tripeptides: Selective conversion into substituted dehydroamino acids

The selective conversion of serine or threonine units of di- and tripeptides into substituted dehydroamino acids is reported. Thus, these common α-amino acids undergo a scission-phosphorylation process to give α-amino phosphonate residues. A Horner-Wadsworth-Emmons reaction with aldehydes or ketones follows to afford the final products with excellent Z-stereoselectivity (Z:E > 98:2). In this way, a single peptide precursor can selectively be transformed into a variety of derivatives.

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Bibliographic Details
Main Authors: Saavedra, Carlos J., Boto, Alicia, Hernández, Rosendo
Other Authors: Ministerio de Ciencia e Innovación (España)
Format: artículo biblioteca
Published: ACS Publications 2012-07-11
Subjects:Selective conversion, Dehydroamino acids, Di- and Tripeptides,
Online Access:http://hdl.handle.net/10261/193405
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100004837
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