A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo

Genetically encoded catalysts for non-natural chemical reactions will open new routes to sustainable production of chemicals. We designed a unique serine-heme ligated cytochrome “P411” that catalyzes efficient and selective carbene transfers from diazoesters to olefins in intact Escherichia coli cel...

Descripción completa

Detalles Bibliográficos
Autores principales: Coelho, Pedro S., Wang, Z. Jane, Ener, Maraia E., Baril, Stefanie A., Kannan, Arvind A., Arnold, Frances H., Brustad, Eric M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3720782/
https://www.ncbi.nlm.nih.gov/pubmed/23792734
http://dx.doi.org/10.1038/nchembio.1278
_version_ 1782277991574798336
author Coelho, Pedro S.
Wang, Z. Jane
Ener, Maraia E.
Baril, Stefanie A.
Kannan, Arvind A.
Arnold, Frances H.
Brustad, Eric M.
author_facet Coelho, Pedro S.
Wang, Z. Jane
Ener, Maraia E.
Baril, Stefanie A.
Kannan, Arvind A.
Arnold, Frances H.
Brustad, Eric M.
author_sort Coelho, Pedro S.
collection PubMed
description Genetically encoded catalysts for non-natural chemical reactions will open new routes to sustainable production of chemicals. We designed a unique serine-heme ligated cytochrome “P411” that catalyzes efficient and selective carbene transfers from diazoesters to olefins in intact Escherichia coli cells. The mutation C400S in cytochrome P450(BM3) gives a signature ferrous-CO Soret peak at 411 nm, abolishes monooxygenation activity, raises the resting state Fe(III/II) reduction potential, and significantly improves NAD(P)H-driven cyclopropanation activity.
format Online
Article
Text
id pubmed-3720782
institution National Center for Biotechnology Information
language English
publishDate 2013
record_format MEDLINE/PubMed
spelling pubmed-37207822014-02-01 A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo Coelho, Pedro S. Wang, Z. Jane Ener, Maraia E. Baril, Stefanie A. Kannan, Arvind A. Arnold, Frances H. Brustad, Eric M. Nat Chem Biol Article Genetically encoded catalysts for non-natural chemical reactions will open new routes to sustainable production of chemicals. We designed a unique serine-heme ligated cytochrome “P411” that catalyzes efficient and selective carbene transfers from diazoesters to olefins in intact Escherichia coli cells. The mutation C400S in cytochrome P450(BM3) gives a signature ferrous-CO Soret peak at 411 nm, abolishes monooxygenation activity, raises the resting state Fe(III/II) reduction potential, and significantly improves NAD(P)H-driven cyclopropanation activity. 2013-06-23 2013-08 /pmc/articles/PMC3720782/ /pubmed/23792734 http://dx.doi.org/10.1038/nchembio.1278 Text en Users may view, print, copy, download and text and data- mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
Coelho, Pedro S.
Wang, Z. Jane
Ener, Maraia E.
Baril, Stefanie A.
Kannan, Arvind A.
Arnold, Frances H.
Brustad, Eric M.
A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title_full A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title_fullStr A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title_full_unstemmed A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title_short A Serine-Substituted P450 Catalyzes Highly Efficient Carbene Transfer to Olefins In Vivo
title_sort serine-substituted p450 catalyzes highly efficient carbene transfer to olefins in vivo
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3720782/
https://www.ncbi.nlm.nih.gov/pubmed/23792734
http://dx.doi.org/10.1038/nchembio.1278
work_keys_str_mv AT coelhopedros aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT wangzjane aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT enermaraiae aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT barilstefaniea aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT kannanarvinda aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT arnoldfrancesh aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT brustadericm aserinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT coelhopedros serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT wangzjane serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT enermaraiae serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT barilstefaniea serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT kannanarvinda serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT arnoldfrancesh serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo
AT brustadericm serinesubstitutedp450catalyzeshighlyefficientcarbenetransfertoolefinsinvivo

Ejemplares similares