Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis

[Image: see text] Bacteria have evolved gibberellin phytohormone biosynthesis independently of plants and fungi. Through (13)C-labeling and NMR analysis, the mechanistically unusual “B” ring contraction catalyzed by a cytochrome P450 (CYP114), which is the committed step in gibberellin biosynthesis,...

Descripción completa

Detalles Bibliográficos
Autores principales: Nett, Ryan S., Dickschat, Jeroen S., Peters, Reuben J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5139915/
https://www.ncbi.nlm.nih.gov/pubmed/27934361
http://dx.doi.org/10.1021/acs.orglett.6b02569
_version_ 1782472329337503744
author Nett, Ryan S.
Dickschat, Jeroen S.
Peters, Reuben J.
author_facet Nett, Ryan S.
Dickschat, Jeroen S.
Peters, Reuben J.
author_sort Nett, Ryan S.
collection PubMed
description [Image: see text] Bacteria have evolved gibberellin phytohormone biosynthesis independently of plants and fungi. Through (13)C-labeling and NMR analysis, the mechanistically unusual “B” ring contraction catalyzed by a cytochrome P450 (CYP114), which is the committed step in gibberellin biosynthesis, was shown to occur via oxidative extrusion of carbon-7 from ent-kaurenoic acid in bacteria. This is identical to the convergently evolved chemical transformation in plants and fungi, suggesting a common semipinacol rearrangement mechanism potentially guided by carbon-4α carboxylate proximity.
format Online
Article
Text
id pubmed-5139915
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-51399152017-11-21 Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis Nett, Ryan S. Dickschat, Jeroen S. Peters, Reuben J. Org Lett [Image: see text] Bacteria have evolved gibberellin phytohormone biosynthesis independently of plants and fungi. Through (13)C-labeling and NMR analysis, the mechanistically unusual “B” ring contraction catalyzed by a cytochrome P450 (CYP114), which is the committed step in gibberellin biosynthesis, was shown to occur via oxidative extrusion of carbon-7 from ent-kaurenoic acid in bacteria. This is identical to the convergently evolved chemical transformation in plants and fungi, suggesting a common semipinacol rearrangement mechanism potentially guided by carbon-4α carboxylate proximity. American Chemical Society 2016-11-21 2016-12-02 /pmc/articles/PMC5139915/ /pubmed/27934361 http://dx.doi.org/10.1021/acs.orglett.6b02569 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Nett, Ryan S.
Dickschat, Jeroen S.
Peters, Reuben J.
Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title_full Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title_fullStr Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title_full_unstemmed Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title_short Labeling Studies Clarify the Committed Step in Bacterial Gibberellin Biosynthesis
title_sort labeling studies clarify the committed step in bacterial gibberellin biosynthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5139915/
https://www.ncbi.nlm.nih.gov/pubmed/27934361
http://dx.doi.org/10.1021/acs.orglett.6b02569
work_keys_str_mv AT nettryans labelingstudiesclarifythecommittedstepinbacterialgibberellinbiosynthesis
AT dickschatjeroens labelingstudiesclarifythecommittedstepinbacterialgibberellinbiosynthesis
AT petersreubenj labelingstudiesclarifythecommittedstepinbacterialgibberellinbiosynthesis

Ejemplares similares