Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes

Autores
Woodcock, Steven; Salvatore, Sonia Rosana; Bonacci, Gustavo Roberto; Schopfer, Francisco; Freemant, Bruce A.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC–MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.
Fil: Woodcock, Steven. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Salvatore, Sonia Rosana. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Bonacci, Gustavo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Schopfer, Francisco. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Freemant, Bruce A.. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Materia
Nitroalkene Synthesis
Reactive Nitrogen Species
Electrophile
Fatty Acid Nitration
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/31953
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated NitrodienesWoodcock, StevenSalvatore, Sonia RosanaBonacci, Gustavo RobertoSchopfer, FranciscoFreemant, Bruce A.Nitroalkene SynthesisReactive Nitrogen SpeciesElectrophileFatty Acid Nitrationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC–MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.Fil: Woodcock, Steven. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados UnidosFil: Salvatore, Sonia Rosana. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados UnidosFil: Bonacci, Gustavo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; ArgentinaFil: Schopfer, Francisco. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados UnidosFil: Freemant, Bruce A.. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados UnidosAmerican Chemical Society2014-01info: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/11336/31953Woodcock, Steven; Salvatore, Sonia Rosana; Bonacci, Gustavo Roberto; Schopfer, Francisco; Freemant, Bruce A.; Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes; American Chemical Society; Journal of Organic Chemistry; 79; 1; 1-2014; 25-330022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo4021562info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/jo4021562info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:50:33Zoai:ri.conicet.gov.ar:11336/31953instacron: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 09:50:33.798CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
title Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
spellingShingle Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
Woodcock, Steven
Nitroalkene Synthesis
Reactive Nitrogen Species
Electrophile
Fatty Acid Nitration
title_short Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
title_full Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
title_fullStr Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
title_full_unstemmed Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
title_sort Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes
dc.creator.none.fl_str_mv Woodcock, Steven
Salvatore, Sonia Rosana
Bonacci, Gustavo Roberto
Schopfer, Francisco
Freemant, Bruce A.
author Woodcock, Steven
author_facet Woodcock, Steven
Salvatore, Sonia Rosana
Bonacci, Gustavo Roberto
Schopfer, Francisco
Freemant, Bruce A.
author_role author
author2 Salvatore, Sonia Rosana
Bonacci, Gustavo Roberto
Schopfer, Francisco
Freemant, Bruce A.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Nitroalkene Synthesis
Reactive Nitrogen Species
Electrophile
Fatty Acid Nitration
topic Nitroalkene Synthesis
Reactive Nitrogen Species
Electrophile
Fatty Acid Nitration
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC–MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.
Fil: Woodcock, Steven. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Salvatore, Sonia Rosana. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Bonacci, Gustavo Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Schopfer, Francisco. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
Fil: Freemant, Bruce A.. Univeristy Of Pittsburgh. School Of Medicine. Department Of Pharmacology And Chemical Biology; Estados Unidos
description Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC–MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/31953
Woodcock, Steven; Salvatore, Sonia Rosana; Bonacci, Gustavo Roberto; Schopfer, Francisco; Freemant, Bruce A.; Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes; American Chemical Society; Journal of Organic Chemistry; 79; 1; 1-2014; 25-33
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31953
identifier_str_mv Woodcock, Steven; Salvatore, Sonia Rosana; Bonacci, Gustavo Roberto; Schopfer, Francisco; Freemant, Bruce A.; Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes; American Chemical Society; Journal of Organic Chemistry; 79; 1; 1-2014; 25-33
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jo4021562
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/jo4021562
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.070432

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