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“Customizable” Units in Di- and Tripeptides: Selective Conversion into Substituted Dehydroamino Acids
- Saavedra, Carlos J., Boto, Alicia, Hernández, Rosendo
- Organic letters 2012 v.14 no.14 pp. 3788-3791
- acids, aldehydes, chemical reactions, chemical structure, ketones, serine, threonine, tripeptides
- 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.