“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...

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Bibliographic Details
Published in:Organic letters 2012-07, Vol.14 (14), p.3788-3791
Main Authors: Saavedra, Carlos J, Boto, Alicia, Hernández, Rosendo
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Dipeptides - chemistry
Molecular Structure
Peptides - chemistry
Phosphorylation
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301676z