"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.
Instituto de Productos Naturales y Agrobiología CSIC , Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
Carlos J
CJ
Saavedra
Alicia
A
Boto
Rosendo
R
Hernández
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010766:Phosphorylation; D013237:Stereoisomerism
D000596:Amino Acids; D004151:Dipeptides; D010455:Peptides