Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis.

ABSTRACT: Carboxylic acids are an important structural feature in many drugs, but are associated with a number of unfavorable pharmacological properties. To address this problem, carboxylic acids can be replaced with bioisosteric mimics that interact similarly with biological targets but avoid these liabilities. Recently, 3-oxetanols have been identified as useful carboxylic acid bioisosteres that maintain similar hydrogen-bonding capacity while decreasing acidity and increasing lipophilicity. However, the installation of 3-oxetanols generally requires multistep de novo synthesis, presenting an obstacle to investigation of these promising bioisosteres. Herein, we report a new synthetic approach involving direct conversion of carboxylic acids to 3-oxetanols using a photoredox-catalyzed decarbo

SUBMITTER: Delos Reyes AMV 

PROVIDER: S-EPMC10548506 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature