Related Experiment Video
Updated: Aug 30, 2026

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
Published on: November 22, 2024
Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides
Marco Molteni1, Alessandro Volonterio, Matteo Zanda
1C.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.
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.
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

