In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C

The antimycobacterial peptides, rufomycins, have their antibiotic activity conferred by oxidative tailoring of the cyclic peptide. Here we elucidate the roles of cytochrome P450s RufS and RufM in regioselective epoxidation and alkyl oxidation respectively and demonstrate how RufM and RufS create a c...

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Autores principales: Perez Ortiz, Gustavo, Sidda, John D., de los Santos, Emmanuel L. C., Hubert, Catherine B., Barry, Sarah M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8577248/
https://www.ncbi.nlm.nih.gov/pubmed/34676855
http://dx.doi.org/10.1039/d1cc04794a
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author Perez Ortiz, Gustavo
Sidda, John D.
de los Santos, Emmanuel L. C.
Hubert, Catherine B.
Barry, Sarah M.
author_facet Perez Ortiz, Gustavo
Sidda, John D.
de los Santos, Emmanuel L. C.
Hubert, Catherine B.
Barry, Sarah M.
author_sort Perez Ortiz, Gustavo
collection PubMed
description The antimycobacterial peptides, rufomycins, have their antibiotic activity conferred by oxidative tailoring of the cyclic peptide. Here we elucidate the roles of cytochrome P450s RufS and RufM in regioselective epoxidation and alkyl oxidation respectively and demonstrate how RufM and RufS create a complex product profile dependent on redox partner availability. Finally, we report the in vitro one pot conversion of rufomycin B to rufomycin C.
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spelling pubmed-85772482021-12-13 In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C Perez Ortiz, Gustavo Sidda, John D. de los Santos, Emmanuel L. C. Hubert, Catherine B. Barry, Sarah M. Chem Commun (Camb) Chemistry The antimycobacterial peptides, rufomycins, have their antibiotic activity conferred by oxidative tailoring of the cyclic peptide. Here we elucidate the roles of cytochrome P450s RufS and RufM in regioselective epoxidation and alkyl oxidation respectively and demonstrate how RufM and RufS create a complex product profile dependent on redox partner availability. Finally, we report the in vitro one pot conversion of rufomycin B to rufomycin C. The Royal Society of Chemistry 2021-10-15 /pmc/articles/PMC8577248/ /pubmed/34676855 http://dx.doi.org/10.1039/d1cc04794a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Perez Ortiz, Gustavo
Sidda, John D.
de los Santos, Emmanuel L. C.
Hubert, Catherine B.
Barry, Sarah M.
In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title_full In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title_fullStr In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title_full_unstemmed In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title_short In vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin B to rufomycin C
title_sort in vitro elucidation of the crucial but complex oxidative tailoring steps in rufomycin biosynthesis enables one pot conversion of rufomycin b to rufomycin c
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8577248/
https://www.ncbi.nlm.nih.gov/pubmed/34676855
http://dx.doi.org/10.1039/d1cc04794a
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