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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/212753
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T09:37:12Zoai: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:34982025-09-29 09:37:13.225CONICET 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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1844613171774488576 |
score |
13.070432 |