A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis

The biosynthesis of photopyrones, novel quorum sensing signals in Photorhabdus, has been studied by heterologous expression of the photopyrone synthase PpyS catalyzing the head-to-head condensation of two acyl moieties. The biochemical mechanism of pyrone formation has been investigated by amino aci...

Descripción completa

Detalles Bibliográficos
Autores principales: Kresovic, Darko, Schempp, Florence, Cheikh-Ali, Zakaria, Bode, Helge B
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578411/
https://www.ncbi.nlm.nih.gov/pubmed/26425196
http://dx.doi.org/10.3762/bjoc.11.152
_version_ 1782391114467115008
author Kresovic, Darko
Schempp, Florence
Cheikh-Ali, Zakaria
Bode, Helge B
author_facet Kresovic, Darko
Schempp, Florence
Cheikh-Ali, Zakaria
Bode, Helge B
author_sort Kresovic, Darko
collection PubMed
description The biosynthesis of photopyrones, novel quorum sensing signals in Photorhabdus, has been studied by heterologous expression of the photopyrone synthase PpyS catalyzing the head-to-head condensation of two acyl moieties. The biochemical mechanism of pyrone formation has been investigated by amino acid exchange and bioinformatic analysis. Additionally, the evolutionary origin of PpyS has been studied by phylogenetic analyses also revealing homologous enzymes in Pseudomonas sp. GM30 responsible for the biosynthesis of pseudopyronines including a novel derivative. Moreover this novel class of ketosynthases is only distantly related to other pyrone-forming enzymes identified in the biosynthesis of the potent antibiotics myxopyronin and corallopyronin.
format Online
Article
Text
id pubmed-4578411
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-45784112015-09-30 A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis Kresovic, Darko Schempp, Florence Cheikh-Ali, Zakaria Bode, Helge B Beilstein J Org Chem Full Research Paper The biosynthesis of photopyrones, novel quorum sensing signals in Photorhabdus, has been studied by heterologous expression of the photopyrone synthase PpyS catalyzing the head-to-head condensation of two acyl moieties. The biochemical mechanism of pyrone formation has been investigated by amino acid exchange and bioinformatic analysis. Additionally, the evolutionary origin of PpyS has been studied by phylogenetic analyses also revealing homologous enzymes in Pseudomonas sp. GM30 responsible for the biosynthesis of pseudopyronines including a novel derivative. Moreover this novel class of ketosynthases is only distantly related to other pyrone-forming enzymes identified in the biosynthesis of the potent antibiotics myxopyronin and corallopyronin. Beilstein-Institut 2015-08-12 /pmc/articles/PMC4578411/ /pubmed/26425196 http://dx.doi.org/10.3762/bjoc.11.152 Text en Copyright © 2015, Kresovic et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kresovic, Darko
Schempp, Florence
Cheikh-Ali, Zakaria
Bode, Helge B
A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title_full A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title_fullStr A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title_full_unstemmed A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title_short A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
title_sort novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578411/
https://www.ncbi.nlm.nih.gov/pubmed/26425196
http://dx.doi.org/10.3762/bjoc.11.152
work_keys_str_mv AT kresovicdarko anovelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT schemppflorence anovelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT cheikhalizakaria anovelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT bodehelgeb anovelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT kresovicdarko novelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT schemppflorence novelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT cheikhalizakaria novelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis
AT bodehelgeb novelandwidespreadclassofketosynthaseisresponsiblefortheheadtoheadcondensationoftwoacylmoietiesinbacterialpyronebiosynthesis

Ejemplares similares