An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis

Autores
Palacio, Cyntia M.; Sabaini, María Belén; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-Monoacetylated derivatives of ribo- (adenosine, guanosine) and 2′-deoxyribonucleosides (2′-deoxyadenosine and 2′-deoxyguanosine), useful as oligonucleotide building blocks, were obtained in 88–100% by enzymatic chemoselective hydrolysis of the corresponding peracetylated nucleosides. Among the tested hydrolases, most satisfactory results were found with acylase I from Aspergillus melleus and Candida antarctica lipase B. For acylase I, the observed chemoselectivity towards ester hydrolysis, without amide reaction, broadens the information about the selectivity of the enzyme and its synthetic applications in the field of nucleosides.
Fil: Palacio, Cyntia M.. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Sabaini, María Belén. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Chemoselectivity
Candida Antarctica Lipase B
Acylase I
Nucleobase N-Protection
Oligonucleotide Building Blocks
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:11336/24092
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysisPalacio, Cyntia M.Sabaini, María BelénIribarren, Adolfo MarceloIglesias, Luis EmilioChemoselectivityCandida Antarctica Lipase BAcylase INucleobase N-ProtectionOligonucleotide Building Blockshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-Monoacetylated derivatives of ribo- (adenosine, guanosine) and 2′-deoxyribonucleosides (2′-deoxyadenosine and 2′-deoxyguanosine), useful as oligonucleotide building blocks, were obtained in 88–100% by enzymatic chemoselective hydrolysis of the corresponding peracetylated nucleosides. Among the tested hydrolases, most satisfactory results were found with acylase I from Aspergillus melleus and Candida antarctica lipase B. For acylase I, the observed chemoselectivity towards ester hydrolysis, without amide reaction, broadens the information about the selectivity of the enzyme and its synthetic applications in the field of nucleosides.Fil: Palacio, Cyntia M.. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; ArgentinaFil: Sabaini, María Belén. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; ArgentinaFil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier2013-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/24092Palacio, Cyntia M.; Sabaini, María Belén; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis; Elsevier; Journal Of Biotechnology; 165; 2; 3-2013; 99-1010168-1656CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jbiotec.2013.03.004info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0168165613001399info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:44Zoai:ri.conicet.gov.ar:11336/24092instacron: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 09:40:44.364CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
title An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
spellingShingle An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
Palacio, Cyntia M.
Chemoselectivity
Candida Antarctica Lipase B
Acylase I
Nucleobase N-Protection
Oligonucleotide Building Blocks
title_short An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
title_full An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
title_fullStr An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
title_full_unstemmed An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
title_sort An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis
dc.creator.none.fl_str_mv Palacio, Cyntia M.
Sabaini, María Belén
Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author Palacio, Cyntia M.
author_facet Palacio, Cyntia M.
Sabaini, María Belén
Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author_role author
author2 Sabaini, María Belén
Iribarren, Adolfo Marcelo
Iglesias, Luis Emilio
author2_role author
author
author
dc.subject.none.fl_str_mv Chemoselectivity
Candida Antarctica Lipase B
Acylase I
Nucleobase N-Protection
Oligonucleotide Building Blocks
topic Chemoselectivity
Candida Antarctica Lipase B
Acylase I
Nucleobase N-Protection
Oligonucleotide Building Blocks
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv N-Monoacetylated derivatives of ribo- (adenosine, guanosine) and 2′-deoxyribonucleosides (2′-deoxyadenosine and 2′-deoxyguanosine), useful as oligonucleotide building blocks, were obtained in 88–100% by enzymatic chemoselective hydrolysis of the corresponding peracetylated nucleosides. Among the tested hydrolases, most satisfactory results were found with acylase I from Aspergillus melleus and Candida antarctica lipase B. For acylase I, the observed chemoselectivity towards ester hydrolysis, without amide reaction, broadens the information about the selectivity of the enzyme and its synthetic applications in the field of nucleosides.
Fil: Palacio, Cyntia M.. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Sabaini, María Belén. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina
Fil: Iglesias, Luis Emilio. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description N-Monoacetylated derivatives of ribo- (adenosine, guanosine) and 2′-deoxyribonucleosides (2′-deoxyadenosine and 2′-deoxyguanosine), useful as oligonucleotide building blocks, were obtained in 88–100% by enzymatic chemoselective hydrolysis of the corresponding peracetylated nucleosides. Among the tested hydrolases, most satisfactory results were found with acylase I from Aspergillus melleus and Candida antarctica lipase B. For acylase I, the observed chemoselectivity towards ester hydrolysis, without amide reaction, broadens the information about the selectivity of the enzyme and its synthetic applications in the field of nucleosides.
publishDate 2013
dc.date.none.fl_str_mv 2013-03
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/11336/24092
Palacio, Cyntia M.; Sabaini, María Belén; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis; Elsevier; Journal Of Biotechnology; 165; 2; 3-2013; 99-101
0168-1656
CONICET Digital
CONICET
url http://hdl.handle.net/11336/24092
identifier_str_mv Palacio, Cyntia M.; Sabaini, María Belén; Iribarren, Adolfo Marcelo; Iglesias, Luis Emilio; An efficient and mild access to N-acetyl protected purine nucleosides based on a chemoselective enzymatic hydrolysis; Elsevier; Journal Of Biotechnology; 165; 2; 3-2013; 99-101
0168-1656
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jbiotec.2013.03.004
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0168165613001399
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
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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