Asymmetric Sulfoxidations Catalyzed by Bacterial Flavin-Containing Monooxygenases

Flavin-containing monooxygenase from Methylophaga sp. (mFMO) was previously discovered to be a valuable biocatalyst used to convert small amines, such as trimethylamine, and various indoles. As FMOs are also known to act on sulfides, we explored mFMO and some mutants thereof for their ability to con...

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Detalhes bibliográficos
Autores: Gonzalo Calvo, Gonzalo de, Coto Cid, Juan Manuel, Lončar, Nikola, Fraaije, Marco W.
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Recursos:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/164959
Acesso em linha:https://hdl.handle.net/11441/164959
https://doi.org/10.3390/molecules29153474
Access Level:acceso abierto
Palavra-chave:Asymmetric oxidations
Biocatalysis
Chiral sulfoxides
Flavin monooxygenases
Descrição
Resumo:Flavin-containing monooxygenase from Methylophaga sp. (mFMO) was previously discovered to be a valuable biocatalyst used to convert small amines, such as trimethylamine, and various indoles. As FMOs are also known to act on sulfides, we explored mFMO and some mutants thereof for their ability to convert prochiral aromatic sulfides. We included a newly identified thermostable FMO obtained from the bacterium Nitrincola lacisaponensis (NiFMO). The FMOs were found to be active with most tested sulfides, forming chiral sulfoxides with moderate-to-high enantioselectivity. Each enzyme variant exhibited a different enantioselective behavior. This shows that small changes in the substrate binding pocket of mFMO influence selectivity, representing a tunable biocatalyst for enantioselective sulfoxidations.