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

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.

SUBMITTER: Pons A

PROVIDER: S-EPMC8851640 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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

Pons Amandine A Decaens Jonathan J Najjar Riham R Otog Nansalmaa N Arribat Mathieu M Jolly Sandrine S Couve-Bonnaire Samuel S Sebban Muriel M Coadou Gael G Oulyadi Hassan H Speybrouck David D Iwasa Seiji S Charette André B AB Poisson Thomas T Jubault Philippe P

ACS omega 20220204 6

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. ...[more]

PMID: 35187307

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