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

AuthorsSaavedra, Carlos J.; Boto, Alicia ; Hernández, Rosendo
KeywordsSelective conversion
Dehydroamino acids
Di- and Tripeptides
Issue Date11-Jul-2012
PublisherACS Publications
CitationOrganic Letters 14(14): 3788-3791 (2012)
AbstractThe 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.
Publisher version (URL)https://pubs.acs.org/doi/10.1021/ol301676z
Identifiersdoi: 10.1021/ol301676z
issn: 1523-7060
e-issn: 1523-7052
Appears in Collections:(IPNA) Artículos
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