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-...
| Published in: | Journal of Molecular Catalysis B: Enzymatic |
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| Main Authors: | , , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
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Elsevier Science
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| Subjects: | |
| Online Access: | http://hdl.handle.net/11336/80102 |
| _version_ | 1821732511420514304 |
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| 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 |
| collection | CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
| container_issue | 1-3 |
| container_start_page | 70 |
| container_title | Journal of Molecular Catalysis B: Enzymatic |
| container_volume | 35 |
| 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 |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| geographic | Argentina Sarmiento Porro Quilmes |
| geographic_facet | Argentina Sarmiento Porro Quilmes |
| id | ftconicet:oai:ri.conicet.gov.ar:11336/80102 |
| institution | Open Polar |
| language | English |
| 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) |
| op_collection_id | ftconicet |
| op_container_end_page | 73 |
| op_doi | https://doi.org/10.1016/j.molcatb.2005.05.010 |
| 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/ |
| publisher | Elsevier Science |
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| spelling | ftconicet:oai:ri.conicet.gov.ar:11336/80102 2025-01-16T19:18:05+00:00 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 |
| 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 |
| title | 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_short | 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 |
| topic | Deacetylation Enzymatic Alcoholysis Lipases Regioselectivity Ribosides https://purl.org/becyt/ford/1.6 https://purl.org/becyt/ford/1 |
| topic_facet | Deacetylation Enzymatic Alcoholysis Lipases Regioselectivity Ribosides https://purl.org/becyt/ford/1.6 https://purl.org/becyt/ford/1 |
| url | http://hdl.handle.net/11336/80102 |