Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides
Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield,...
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Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_10242422_v28_n4_p267_Gudino |
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todo:paper_10242422_v28_n4_p267_Gudino2023-10-03T15:56:52Z Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides Gudiño, E.D. Iribarren, A.M. Iglesias, L.E. Candida antarctica B lipase Enzymatic alcoholysis Regioselectivity Ribofuranosides Alcoholysis Anomerics Candida antarctica B Candida antarctica B lipase Enzymatic alcoholysis Enzymatic deacetylation N-propyl Acetylation Alkylation Catalysis Hydrocarbons Regioselectivity Yeast Isomers alcohol carbohydrate derivative dextro ribofuranoside derivative lipase B unclassified drug alcoholysis article Candida antarctica catalysis chemical structure deacetylation enzyme substrate Candida antarctica Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity. © 2010 Informa UK Ltd. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10242422_v28_n4_p267_Gudino |
institution |
Universidad de Buenos Aires |
institution_str |
I-28 |
repository_str |
R-134 |
collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
topic |
Candida antarctica B lipase Enzymatic alcoholysis Regioselectivity Ribofuranosides Alcoholysis Anomerics Candida antarctica B Candida antarctica B lipase Enzymatic alcoholysis Enzymatic deacetylation N-propyl Acetylation Alkylation Catalysis Hydrocarbons Regioselectivity Yeast Isomers alcohol carbohydrate derivative dextro ribofuranoside derivative lipase B unclassified drug alcoholysis article Candida antarctica catalysis chemical structure deacetylation enzyme substrate Candida antarctica |
spellingShingle |
Candida antarctica B lipase Enzymatic alcoholysis Regioselectivity Ribofuranosides Alcoholysis Anomerics Candida antarctica B Candida antarctica B lipase Enzymatic alcoholysis Enzymatic deacetylation N-propyl Acetylation Alkylation Catalysis Hydrocarbons Regioselectivity Yeast Isomers alcohol carbohydrate derivative dextro ribofuranoside derivative lipase B unclassified drug alcoholysis article Candida antarctica catalysis chemical structure deacetylation enzyme substrate Candida antarctica Gudiño, E.D. Iribarren, A.M. Iglesias, L.E. Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
topic_facet |
Candida antarctica B lipase Enzymatic alcoholysis Regioselectivity Ribofuranosides Alcoholysis Anomerics Candida antarctica B Candida antarctica B lipase Enzymatic alcoholysis Enzymatic deacetylation N-propyl Acetylation Alkylation Catalysis Hydrocarbons Regioselectivity Yeast Isomers alcohol carbohydrate derivative dextro ribofuranoside derivative lipase B unclassified drug alcoholysis article Candida antarctica catalysis chemical structure deacetylation enzyme substrate Candida antarctica |
description |
Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl α, β-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-α, β-D-ribofuranosides enriched in the α-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-β-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl α, β-D-ribofuranosides reacted without selectivity. © 2010 Informa UK Ltd. |
format |
JOUR |
author |
Gudiño, E.D. Iribarren, A.M. Iglesias, L.E. |
author_facet |
Gudiño, E.D. Iribarren, A.M. Iglesias, L.E. |
author_sort |
Gudiño, E.D. |
title |
Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
title_short |
Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
title_full |
Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
title_fullStr |
Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
title_full_unstemmed |
Candida antarctica B lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides |
title_sort |
candida antarctica b lipase-catalysed alcoholysis of peracetylated alkyl d-ribofuranosides |
url |
http://hdl.handle.net/20.500.12110/paper_10242422_v28_n4_p267_Gudino |
work_keys_str_mv |
AT gudinoed candidaantarcticablipasecatalysedalcoholysisofperacetylatedalkyldribofuranosides AT iribarrenam candidaantarcticablipasecatalysedalcoholysisofperacetylatedalkyldribofuranosides AT iglesiasle candidaantarcticablipasecatalysedalcoholysisofperacetylatedalkyldribofuranosides |
_version_ |
1782030576162701312 |