title: Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides.
abstract: [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.
authors.affiliation: 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.
authors.forename: Marco
authors.initials: M
authors.lastname: Molteni
authors.forename: Alessandro
authors.initials: A
authors.lastname: Volonterio
authors.forename: Matteo
authors.initials: M
authors.lastname: Zanda
mesh_terms: D008956:Models, Chemical; D018716:Molecular Mimicry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides