Abstract:
A set of eight mono-, di-, tri- and tetraalkoxycarbonylated nucleosides was tested in order to assess their enzymatic hydrolysis. All the alkoxycarbonyl groups of the assayed substrates, from both carbonate and carbamate functions, were quantitatively hydrolysed using pig liver esterase (PLE) at pH 7 and 60°C, regardless of the nucleoside base. Quantitative full alkoxycarbonyl groups removal was also reached by Candida antarctica B lipase (CAL B) under mild conditions, but in this case, longer reaction times were required. Thus, PLE appears as an useful catalyst for the mild and quantitative deprotection of nucleoside carbonates and carbamates in the synthesis of modified nucleosides. © 2005 Elsevier B.V. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase |
Autor: | Capello, M.; González, M.; Rodríguez, S.D.; Iglesias, L.E.; Iribarren, A.M. |
Filiación: | Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 180, 1876 Bernal, Argentina INGEBI (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina
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Palabras clave: | Carbamates; Carbonates; Deprotection; Hydrolases; Nucleosides; Enzymes; Hydrolysis; Substrates; Synthesis (chemical); Carbamates; Deprotection; Hydrolases; Nucleosides; Carbonates; carbamic acid; carbonic acid; carbonyl derivative; esterase; liver enzyme; nucleoside derivative; triacylglycerol lipase; article; Candida antarctica; carbonylation; catalyst; controlled study; hydrolysis kinetics; nonhuman; pH measurement; quantitative analysis; temperature dependence; Candida antarctica; Sus scrofa |
Año: | 2005
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Volumen: | 36
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Número: | 1-6
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Página de inicio: | 36
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Página de fin: | 39
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DOI: |
http://dx.doi.org/10.1016/j.molcatb.2005.08.001 |
Título revista: | Journal of Molecular Catalysis B: Enzymatic
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Título revista abreviado: | J. Mol. Catal. B Enzym.
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ISSN: | 13811177
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CODEN: | JMCEF
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CAS: | carbamic acid, 463-77-4; carbonic acid, 3812-32-6, 463-79-6; esterase, 9013-79-0; triacylglycerol lipase, 9001-62-1
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v36_n1-6_p36_Capello |
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Citas:
---------- APA ----------
Capello, M., González, M., Rodríguez, S.D., Iglesias, L.E. & Iribarren, A.M.
(2005)
. A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase. Journal of Molecular Catalysis B: Enzymatic, 36(1-6), 36-39.
http://dx.doi.org/10.1016/j.molcatb.2005.08.001---------- CHICAGO ----------
Capello, M., González, M., Rodríguez, S.D., Iglesias, L.E., Iribarren, A.M.
"A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase"
. Journal of Molecular Catalysis B: Enzymatic 36, no. 1-6
(2005) : 36-39.
http://dx.doi.org/10.1016/j.molcatb.2005.08.001---------- MLA ----------
Capello, M., González, M., Rodríguez, S.D., Iglesias, L.E., Iribarren, A.M.
"A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase"
. Journal of Molecular Catalysis B: Enzymatic, vol. 36, no. 1-6, 2005, pp. 36-39.
http://dx.doi.org/10.1016/j.molcatb.2005.08.001---------- VANCOUVER ----------
Capello, M., González, M., Rodríguez, S.D., Iglesias, L.E., Iribarren, A.M. A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase. J. Mol. Catal. B Enzym. 2005;36(1-6):36-39.
http://dx.doi.org/10.1016/j.molcatb.2005.08.001