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Flavin Metallaphotoredox Catalysis: Synergistic Synthesis in Water.

ABSTRACT: Combining a transition metal with a photocatalyst can drive modern synthetic chemistry. For transformations performed in water, this concept has been largely unexplored. We report the successful merger of a biocompatible flavin photocatalyst with a palladium catalyst to build isotopically enriched peptidomimetics, to mediate conjugate addition and C-H functionalization reactions, and to assemble unprotected proteinogenic and nonproteinogenic peptides, in water. We detail the important role of the ligand and the palladium oxidation state for controlling product selectivity when constructing synthetic peptides.

SUBMITTER: Chilamari M

PROVIDER: S-EPMC9299445 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Flavin Metallaphotoredox Catalysis: Synergistic Synthesis in Water.

Chilamari Maheshwerreddy M Immel Jacob R JR Chen Pei-Hsuan PH Alghafli Bayan M BM Bloom Steven S

ACS catalysis 20220322 7

Combining a transition metal with a photocatalyst can drive modern synthetic chemistry. For transformations performed in water, this concept has been largely unexplored. We report the successful merger of a biocompatible flavin photocatalyst with a palladium catalyst to build isotopically enriched peptidomimetics, to mediate conjugate addition and <i>C-H</i> functionalization reactions, and to assemble unprotected proteinogenic and nonproteinogenic peptides, in water. We detail the important rol ...[more]

PMID: 35865831

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