An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates

Autores
Gudiño, Esteban Dario; Santillan, Julia Yamila; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new procedure was carried out for the synthesis of nucleoside 5′-monophosphates, involving the use of two enzymes. The first step applied phospholipase D from Streptomyces netropsis and phosphatidylcholine as phosphatidyl donor, to give 5′-(3-sn-phosphatidyl) nucleosides (C, U, A, I). These were selectively hydrolysed in the second step by the action of phospholipase C from Bacillus cereus to produce the respective 5′-nucleotides. Application of this methodology on a preparative scale conducted to 5′-adenosine monophosphate in 63% overall yield from adenosine. The regioselectivity of these enzymes avoids protection steps, the overall synthesis is performed under mild reaction conditions and product isolation is easily achieved.
Fil: Gudiño, Esteban Dario. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina
Fil: Santillan, Julia Yamila. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
BIOCATALYSIS
NUCLEOSIDE 5′-MONOPHOSPHATES
NUCLEOSIDES
PHOSPHODIESTERASES
PHOSPHOLIPASES
PHOSPHORYLATION
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:11336/99164
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/99164
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling An enzymatic alternative for the synthesis of nucleoside 5′-monophosphatesGudiño, Esteban DarioSantillan, Julia YamilaIglesias, Luis EmilioIribarren, Adolfo MarceloBIOCATALYSISNUCLEOSIDE 5′-MONOPHOSPHATESNUCLEOSIDESPHOSPHODIESTERASESPHOSPHOLIPASESPHOSPHORYLATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new procedure was carried out for the synthesis of nucleoside 5′-monophosphates, involving the use of two enzymes. The first step applied phospholipase D from Streptomyces netropsis and phosphatidylcholine as phosphatidyl donor, to give 5′-(3-sn-phosphatidyl) nucleosides (C, U, A, I). These were selectively hydrolysed in the second step by the action of phospholipase C from Bacillus cereus to produce the respective 5′-nucleotides. Application of this methodology on a preparative scale conducted to 5′-adenosine monophosphate in 63% overall yield from adenosine. The regioselectivity of these enzymes avoids protection steps, the overall synthesis is performed under mild reaction conditions and product isolation is easily achieved.Fil: Gudiño, Esteban Dario. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; ArgentinaFil: Santillan, Julia Yamila. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; ArgentinaFil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science Inc2018-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/99164Gudiño, Esteban Dario; Santillan, Julia Yamila; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates; Elsevier Science Inc; Enzyme and Microbial Technology; 111; 4-2018; 1-60141-0229CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0141022917302399info:eu-repo/semantics/altIdentifier/doi/10.1016/j.enzmictec.2017.12.004info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:35:05Zoai:ri.conicet.gov.ar:11336/99164instacron: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 09:35:05.853CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
title An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
spellingShingle An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
Gudiño, Esteban Dario
BIOCATALYSIS
NUCLEOSIDE 5′-MONOPHOSPHATES
NUCLEOSIDES
PHOSPHODIESTERASES
PHOSPHOLIPASES
PHOSPHORYLATION
title_short An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
title_full An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
title_fullStr An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
title_full_unstemmed An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
title_sort An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates
dc.creator.none.fl_str_mv Gudiño, Esteban Dario
Santillan, Julia Yamila
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author Gudiño, Esteban Dario
author_facet Gudiño, Esteban Dario
Santillan, Julia Yamila
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author_role author
author2 Santillan, Julia Yamila
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author2_role author
author
author
dc.subject.none.fl_str_mv BIOCATALYSIS
NUCLEOSIDE 5′-MONOPHOSPHATES
NUCLEOSIDES
PHOSPHODIESTERASES
PHOSPHOLIPASES
PHOSPHORYLATION
topic BIOCATALYSIS
NUCLEOSIDE 5′-MONOPHOSPHATES
NUCLEOSIDES
PHOSPHODIESTERASES
PHOSPHOLIPASES
PHOSPHORYLATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new procedure was carried out for the synthesis of nucleoside 5′-monophosphates, involving the use of two enzymes. The first step applied phospholipase D from Streptomyces netropsis and phosphatidylcholine as phosphatidyl donor, to give 5′-(3-sn-phosphatidyl) nucleosides (C, U, A, I). These were selectively hydrolysed in the second step by the action of phospholipase C from Bacillus cereus to produce the respective 5′-nucleotides. Application of this methodology on a preparative scale conducted to 5′-adenosine monophosphate in 63% overall yield from adenosine. The regioselectivity of these enzymes avoids protection steps, the overall synthesis is performed under mild reaction conditions and product isolation is easily achieved.
Fil: Gudiño, Esteban Dario. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina
Fil: Santillan, Julia Yamila. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description A new procedure was carried out for the synthesis of nucleoside 5′-monophosphates, involving the use of two enzymes. The first step applied phospholipase D from Streptomyces netropsis and phosphatidylcholine as phosphatidyl donor, to give 5′-(3-sn-phosphatidyl) nucleosides (C, U, A, I). These were selectively hydrolysed in the second step by the action of phospholipase C from Bacillus cereus to produce the respective 5′-nucleotides. Application of this methodology on a preparative scale conducted to 5′-adenosine monophosphate in 63% overall yield from adenosine. The regioselectivity of these enzymes avoids protection steps, the overall synthesis is performed under mild reaction conditions and product isolation is easily achieved.
publishDate 2018
dc.date.none.fl_str_mv 2018-04
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/11336/99164
Gudiño, Esteban Dario; Santillan, Julia Yamila; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates; Elsevier Science Inc; Enzyme and Microbial Technology; 111; 4-2018; 1-6
0141-0229
CONICET Digital
CONICET
url http://hdl.handle.net/11336/99164
identifier_str_mv Gudiño, Esteban Dario; Santillan, Julia Yamila; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; An enzymatic alternative for the synthesis of nucleoside 5′-monophosphates; Elsevier Science Inc; Enzyme and Microbial Technology; 111; 4-2018; 1-6
0141-0229
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://www.sciencedirect.com/science/article/pii/S0141022917302399
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.enzmictec.2017.12.004
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
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
_version_ 1844613089956200448
score 13.070432

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