Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides

Marco Molteni; Alessandro Volonterio; Matteo Zanda

doi:10.1021/ol0354730

Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides

Org Lett. 2003 Oct 16;5(21):3887-90. doi: 10.1021/ol0354730.

Authors

Marco Molteni¹, Alessandro Volonterio, Matteo Zanda

Affiliation

¹ 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.

PMID: 14535735
DOI: 10.1021/ol0354730

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Models, Chemical
Molecular Mimicry
Molecular Structure
Oligopeptides / chemical synthesis*
Oligopeptides / chemistry
Stereoisomerism

Substances

Oligopeptides