Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC

Autores
Fries, Alexander Erich; Mazzaferro, Laura; Bisel, Philippe; Hubrich, Florian; Andexer, Jennifer N.; Müller, Michael
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the biosynthesis of menaquinone in bacteria, the thiamine diphosphate-dependent enzyme MenD catalyzes the decarboxylative carboligation of α-ketoglutarate and isochorismate to (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC). The regioisomer of SEPHCHC, namely (1R,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-2-ene-1-carboxylate (iso-SEPHCHC), has been considered as a possible product, however, its existence has been doubtful due to a spontaneous elimination of pyruvate from SEPHCHC to 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC). In this work, the regioisomer iso-SEPHCHC was distinguished from SEPHCHC by liquid chromatography-tandem mass spectrometry. Iso-SEPHCHC was purified and identified by NMR spectroscopy. Just as SEPHCHC remained hidden as a MenD product for more than two decades, its regioisomer iso-SEPHCHC has remained until now.
Fil: Fries, Alexander Erich. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; Alemania
Fil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; Alemania
Fil: Bisel, Philippe. Albert Ludwigs University of Freiburg; Alemania
Fil: Hubrich, Florian. Albert Ludwigs University of Freiburg; Alemania
Fil: Andexer, Jennifer N.. Albert Ludwigs University of Freiburg; Alemania
Fil: Müller, Michael. Albert Ludwigs University of Freiburg; Alemania
Materia
CHORISMATE
C−C COUPLING
ENZYMES
STETTER REACTION
THIAMINE
UMPOLUNG
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/212753
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/212753
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHCFries, Alexander ErichMazzaferro, LauraBisel, PhilippeHubrich, FlorianAndexer, Jennifer N.Müller, MichaelCHORISMATEC−C COUPLINGENZYMESSTETTER REACTIONTHIAMINEUMPOLUNGhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2In the biosynthesis of menaquinone in bacteria, the thiamine diphosphate-dependent enzyme MenD catalyzes the decarboxylative carboligation of α-ketoglutarate and isochorismate to (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC). The regioisomer of SEPHCHC, namely (1R,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-2-ene-1-carboxylate (iso-SEPHCHC), has been considered as a possible product, however, its existence has been doubtful due to a spontaneous elimination of pyruvate from SEPHCHC to 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC). In this work, the regioisomer iso-SEPHCHC was distinguished from SEPHCHC by liquid chromatography-tandem mass spectrometry. Iso-SEPHCHC was purified and identified by NMR spectroscopy. Just as SEPHCHC remained hidden as a MenD product for more than two decades, its regioisomer iso-SEPHCHC has remained until now.Fil: Fries, Alexander Erich. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; AlemaniaFil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; AlemaniaFil: Bisel, Philippe. Albert Ludwigs University of Freiburg; AlemaniaFil: Hubrich, Florian. Albert Ludwigs University of Freiburg; AlemaniaFil: Andexer, Jennifer N.. Albert Ludwigs University of Freiburg; AlemaniaFil: Müller, Michael. Albert Ludwigs University of Freiburg; AlemaniaWiley VCH Verlag2022-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/212753Fries, Alexander Erich; Mazzaferro, Laura; Bisel, Philippe; Hubrich, Florian; Andexer, Jennifer N.; et al.; Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC; Wiley VCH Verlag; Chembiochem; 23; 18; 7-2022; 1-41439-4227CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.202200181info:eu-repo/semantics/altIdentifier/doi/10.1002/cbic.202200181info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:05:22Zoai:ri.conicet.gov.ar:11336/212753instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:05:22.294CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
title Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
spellingShingle Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
Fries, Alexander Erich
CHORISMATE
C−C COUPLING
ENZYMES
STETTER REACTION
THIAMINE
UMPOLUNG
title_short Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
title_full Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
title_fullStr Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
title_full_unstemmed Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
title_sort Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC
dc.creator.none.fl_str_mv Fries, Alexander Erich
Mazzaferro, Laura
Bisel, Philippe
Hubrich, Florian
Andexer, Jennifer N.
Müller, Michael
author Fries, Alexander Erich
author_facet Fries, Alexander Erich
Mazzaferro, Laura
Bisel, Philippe
Hubrich, Florian
Andexer, Jennifer N.
Müller, Michael
author_role author
author2 Mazzaferro, Laura
Bisel, Philippe
Hubrich, Florian
Andexer, Jennifer N.
Müller, Michael
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv CHORISMATE
C−C COUPLING
ENZYMES
STETTER REACTION
THIAMINE
UMPOLUNG
topic CHORISMATE
C−C COUPLING
ENZYMES
STETTER REACTION
THIAMINE
UMPOLUNG
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In the biosynthesis of menaquinone in bacteria, the thiamine diphosphate-dependent enzyme MenD catalyzes the decarboxylative carboligation of α-ketoglutarate and isochorismate to (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC). The regioisomer of SEPHCHC, namely (1R,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-2-ene-1-carboxylate (iso-SEPHCHC), has been considered as a possible product, however, its existence has been doubtful due to a spontaneous elimination of pyruvate from SEPHCHC to 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC). In this work, the regioisomer iso-SEPHCHC was distinguished from SEPHCHC by liquid chromatography-tandem mass spectrometry. Iso-SEPHCHC was purified and identified by NMR spectroscopy. Just as SEPHCHC remained hidden as a MenD product for more than two decades, its regioisomer iso-SEPHCHC has remained until now.
Fil: Fries, Alexander Erich. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; Alemania
Fil: Mazzaferro, Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias de la Tierra y Ambientales de La Pampa. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de La Pampa; Argentina. Albert Ludwigs University of Freiburg; Alemania
Fil: Bisel, Philippe. Albert Ludwigs University of Freiburg; Alemania
Fil: Hubrich, Florian. Albert Ludwigs University of Freiburg; Alemania
Fil: Andexer, Jennifer N.. Albert Ludwigs University of Freiburg; Alemania
Fil: Müller, Michael. Albert Ludwigs University of Freiburg; Alemania
description In the biosynthesis of menaquinone in bacteria, the thiamine diphosphate-dependent enzyme MenD catalyzes the decarboxylative carboligation of α-ketoglutarate and isochorismate to (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC). The regioisomer of SEPHCHC, namely (1R,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-2-ene-1-carboxylate (iso-SEPHCHC), has been considered as a possible product, however, its existence has been doubtful due to a spontaneous elimination of pyruvate from SEPHCHC to 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC). In this work, the regioisomer iso-SEPHCHC was distinguished from SEPHCHC by liquid chromatography-tandem mass spectrometry. Iso-SEPHCHC was purified and identified by NMR spectroscopy. Just as SEPHCHC remained hidden as a MenD product for more than two decades, its regioisomer iso-SEPHCHC has remained until now.
publishDate 2022
dc.date.none.fl_str_mv 2022-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/212753
Fries, Alexander Erich; Mazzaferro, Laura; Bisel, Philippe; Hubrich, Florian; Andexer, Jennifer N.; et al.; Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC; Wiley VCH Verlag; Chembiochem; 23; 18; 7-2022; 1-4
1439-4227
CONICET Digital
CONICET
url http://hdl.handle.net/11336/212753
identifier_str_mv Fries, Alexander Erich; Mazzaferro, Laura; Bisel, Philippe; Hubrich, Florian; Andexer, Jennifer N.; et al.; Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC; Wiley VCH Verlag; Chembiochem; 23; 18; 7-2022; 1-4
1439-4227
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.202200181
info:eu-repo/semantics/altIdentifier/doi/10.1002/cbic.202200181
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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