Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers

The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-...

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Published in:Journal of Molecular Catalysis B: Enzymatic
Main Authors: Iñigo, Sabrina, Taverna Porro, Marisa Lia, Montserrat, Javier Marcelo, Iglesias, Luis Emilio, Iribarren, Adolfo Marcelo
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier Science
Subjects:
Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
Argentina
Sarmiento
Porro
Quilmes
Antarc*
Antarctica
Online Access:http://hdl.handle.net/11336/80102
id ftconicet:oai:ri.conicet.gov.ar:11336/80102
record_format openpolar
spelling ftconicet:oai:ri.conicet.gov.ar:11336/80102 2023-10-09T21:45:45+02:00 Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers Iñigo, Sabrina Taverna Porro, Marisa Lia Montserrat, Javier Marcelo Iglesias, Luis Emilio Iribarren, Adolfo Marcelo application/pdf http://hdl.handle.net/11336/80102 eng eng Elsevier Science info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117705000809 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2005.05.010 http://hdl.handle.net/11336/80102 Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 35; 1-3; 8-2005; 70-73 1381-1177 CONICET Digital CONICET info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ Deacetylation Enzymatic Alcoholysis Lipases Regioselectivity Ribosides https://purl.org/becyt/ford/1.6 https://purl.org/becyt/ford/1 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet https://doi.org/10.1016/j.molcatb.2005.05.010 2023-09-24T18:36:12Z The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days). Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina Fil: Montserrat, Javier 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 General Sarmiento. Instituto de Ciencias; Argentina Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; 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; Argentina Article in Journal/Newspaper Antarc* Antarctica CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Sarmiento ENVELOPE(-68.000,-68.000,-72.000,-72.000) Porro ENVELOPE(23.567,23.567,65.517,65.517) Quilmes ENVELOPE(-55.617,-55.617,-63.233,-63.233) Journal of Molecular Catalysis B: Enzymatic 35 1-3 70 73
institution Open Polar
collection CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas)
op_collection_id ftconicet
language English
topic Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
spellingShingle Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
Iñigo, Sabrina
Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
topic_facet Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
description The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days). Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina Fil: Montserrat, Javier 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 General Sarmiento. Instituto de Ciencias; Argentina Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; 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; Argentina
format Article in Journal/Newspaper
author Iñigo, Sabrina
Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author_facet Iñigo, Sabrina
Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author_sort Iñigo, Sabrina
title Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_short Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_full Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_fullStr Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_full_unstemmed Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_sort deprotection of peracetylated methyl d-ribosides through enzymatic alcoholysis: different recognition of the anomers
publisher Elsevier Science
url http://hdl.handle.net/11336/80102
long_lat ENVELOPE(-68.000,-68.000,-72.000,-72.000)
ENVELOPE(23.567,23.567,65.517,65.517)
ENVELOPE(-55.617,-55.617,-63.233,-63.233)
geographic Argentina
Sarmiento
Porro
Quilmes
geographic_facet Argentina
Sarmiento
Porro
Quilmes
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_relation info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117705000809
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2005.05.010
http://hdl.handle.net/11336/80102
Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 35; 1-3; 8-2005; 70-73
1381-1177
CONICET Digital
CONICET
op_rights info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
op_doi https://doi.org/10.1016/j.molcatb.2005.05.010
container_title Journal of Molecular Catalysis B: Enzymatic
container_volume 35
container_issue 1-3
container_start_page 70
op_container_end_page 73
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