Work

Pyridoxal‐Inspired Photo‐Decarboxylase Catalysis: Photochemical Decarboxylation of Unprotected Amino Acids

Year: 2025

Type: article

Abstract: A photochemical organocatalytic method for the protodecarboxylation of unprotected amino acids is reported. Inspired by pyridoxal 5'-phosphate-dependent decarboxylase enzymes, the catalytic activation of amino acid substrates by 3-hydroxyisonicotinaldehyde enables a photochemical decarboxylation event, which can be leveraged in combination with a thiol co-catalyst. The necessary and sufficient structural features of the pyridoxal-like framework for photoactivity are determined using ultraviolet-visible absorption spectroscopy. A broad scope of unprotected amino acids can be decarboxylated in this system, with selectivity between multiple carboxylates realized on the possible basis of hyperconjugation. The ability to engage simple amino acids in decarboxylative functionalization at ambient conditions using a pyridoxal-mimicking organocatalyst enables new possibilities for the translation of biogenic amino acids into medicinally valuable amines.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202424843

Authors: Dong‐Hang Tan, Agniva Das, Vincent Huang, Timothy D. Schoch, Abubakar Lawal Mohammed, Jeffrey M. Lipshultz

Institution: Stony Brook University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: American Chemical Society Green Chemistry Institute Pharmaceutical Roundtable, National Institute of General Medical Sciences

Awards: G1280615454, G7079796644