Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemist's Toolbox

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Feb 21

PMID 35187307

Authors

Amandine Pons

Jonathan Decaens

Riham Najjar

Nansalmaa Otog

Mathieu Arribat

Sandrine Jolly

Samuel Couve-Bonnaire

Muriel Sebban

Gael Coadou

Hassan Oulyadi

David Speybrouck

Seiji Iwasa

Andre B Charette

Thomas Poisson

Philippe Jubault

Affiliations

Soon will be listed here.

Abstract

Over the years, numerous modifications to the structure of proline have been made in order to tune its effects on bioactive compounds. Notably, the introduction of a cyclopropane ring or a fluorine atom has produced interesting results. Herein, we describe the synthesis of a proline containing fluorocyclopropane. This modified amino acid was inserted into a tripeptide, whose conformation was studied by nuclear magnetic resonance and density functional theory calculations.

Citing Articles

Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles.

Li J, Zhang Z, Chen L, Li M, Zhang X, Zhang G Molecules. 2023; 28(9).

PMID: 37175101 PMC: 10179847. DOI: 10.3390/molecules28093691.

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