Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides.
[reaction: see text] A novel class of peptidomimetics having a stereogenic [CH(CF(3))NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled aza-Michael addition of chiral alpha-amino acid esters to trans-3,3,3-trifluoro-1-nitropropene. The stereoselectivity is strongly influenced by the solvent, the base, its stoichiometry, and the R side-chain. Diastereomeric ratios higher than 11:1 were achieved using H-Val-OtBu.HCl in toluene with 1.1 equiv of DIPEA.
Molteni
Marco
M
C.N.R.-Istituto di Chimica del Riconoscimento Molecolare, sezione A. Quilico, and Dipartimento di Chimica, Materiali ed Ingegneria Chimica G. Natta, Politecnico di Milano, via Mancinelli 7, I-20131, Milan, Italy.
Volonterio
Alessandro
A
Zanda
Matteo
M
D008956:Models, Chemical; D018716:Molecular Mimicry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009842:Oligopeptides