Preparation of potential 3-deazauridine and 6-azauridine prodrugs through an enzymatic alcoholysis
A set of 3-deazauridine and 6-azauridine peracylated derivatives were regioselectively deacylated through Candida antarctica B lipase (CAL B) catalysed alcoholysis. This biotransformation provided an access to six new 2′,3′-di-O-acylated derivatives of 3-deazauridine and 6-azauridine carrying acetyl...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2007
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 06779caa a22010457a 4500 | ||
|---|---|---|---|
| 001 | PAPER-22653 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205414.0 | ||
| 008 | 190411s2007 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-34249706320 | |
| 024 | 7 | |2 cas |a 3 deazauridine, 23205-42-7; azauridine, 54-25-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCEF | ||
| 100 | 1 | |a Zinni, M.A. | |
| 245 | 1 | 0 | |a Preparation of potential 3-deazauridine and 6-azauridine prodrugs through an enzymatic alcoholysis |
| 260 | |c 2007 | ||
| 270 | 1 | 0 | |m Iglesias, L.E.; Departamento de Ciencia y Tecnología, Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 352, Bernal, Provincia de Buenos Aires, Argentina; email: leiglesias@unq.edu.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Manfredini, S., Baraldi, P.G., Bazzanini, R., Bortolotti, F., Vertuani, S., Ashida, N., Machida, H., (1998) Antivir. Chem. Chemother., 9, p. 25 | ||
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| 504 | |a Tamarez, M., Morgan, B., Wong, G.S.K., Tong, W., Bennett, F., Lovey, R., McCormick, J.L., Zaks, A., (2003) Org. Process. Res. Dev., 7, p. 951 | ||
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| 504 | |a Kadereit, D., Waldmann, H., (2001) Chem. Rev., 101, p. 3367 | ||
| 504 | |a Iglesias, L.E., Zinni, M.A., Gallo, M., Iribarren, A.M., (2000) Biotechnol. Lett., 22, p. 361 | ||
| 504 | |a Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E., Iribarren, A.M., (2001) Biotechnol. Lett., 23, p. 1439 | ||
| 504 | |a Zinni, M.A., Iglesias, L.E., Iribarren, A.M., (2002) Biotechnol. Lett., 24, p. 979 | ||
| 504 | |a Zinni, M.A., Rodríguez, S.D., Pontiggia, R.M., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M., (2004) J. Mol. Catal. B: Enzym., 29, p. 129 | ||
| 504 | |a Matzuda, A., Shinozaki, M., Suzuki, M., Watanabe, K., Miyasaka, T., (1986) Synthesis, p. 385 | ||
| 504 | |a Zinni, M.A., Aljinovic, E., Iglesias, L.E., Iribarren, A.M., (2004) Quim. Nova, 27, p. 496 | ||
| 520 | 3 | |a A set of 3-deazauridine and 6-azauridine peracylated derivatives were regioselectively deacylated through Candida antarctica B lipase (CAL B) catalysed alcoholysis. This biotransformation provided an access to six new 2′,3′-di-O-acylated derivatives of 3-deazauridine and 6-azauridine carrying acetyl, butanoyl or hexanoyl moieties, which were obtained in 80-99% yield. The regioselectivity displayed by CAL B towards 5′-O-acyl group removal agrees with the previously reported behavior of this enzyme in the acylation and deacylation of nucleosides. Log P, aqueous solubility and aqueous stability of these new diacylated compounds were determined, suggesting that the dibutanoylated and the dihexanoylated derivatives of 3-deazauridine and 6-azauridine could potentially act as prodrugs of the parent pharmacological active nucleosides. © 2007 Elsevier B.V. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad Nacional de Quilmes | ||
| 536 | |a Detalles de la financiación: Secretaria de Ciencia y Tecnica, Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Centro de Investigación en Computación | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We thank UNQ, CONICET, SECyT and CIC for partial financial support. LEI and AMI are research members of CONICET. We are grateful to Novozymes (Brazil) for the generous gift of CAL B. | ||
| 593 | |a Departamento de Ciencia y Tecnología, Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 352, Bernal, Provincia de Buenos Aires, Argentina | ||
| 593 | |a INGEBI (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ENZYMATIC ALCOHOLYSIS |
| 690 | 1 | 0 | |a LIPASE |
| 690 | 1 | 0 | |a NUCLEOSIDES |
| 690 | 1 | 0 | |a PRODRUGS |
| 690 | 1 | 0 | |a REGIOSELECTIVITY |
| 690 | 1 | 0 | |a ACYLATION |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a DERIVATIVES |
| 690 | 1 | 0 | |a ENZYME ACTIVITY |
| 690 | 1 | 0 | |a REGIOSELECTIVITY |
| 690 | 1 | 0 | |a AQUEOUS SOLUBILITY |
| 690 | 1 | 0 | |a BIOTRANSFORMATION |
| 690 | 1 | 0 | |a DEACYLATION |
| 690 | 1 | 0 | |a NUCLEOSIDES |
| 690 | 1 | 0 | |a PRODRUGS |
| 690 | 1 | 0 | |a DRUG PRODUCTS |
| 690 | 1 | 0 | |a 3 DEAZAURIDINE |
| 690 | 1 | 0 | |a AZAURIDINE |
| 690 | 1 | 0 | |a LIPASE B |
| 690 | 1 | 0 | |a NUCLEOSIDE DERIVATIVE |
| 690 | 1 | 0 | |a PRODRUG |
| 690 | 1 | 0 | |a ALCOHOLYSIS |
| 690 | 1 | 0 | |a AQUEOUS SOLUTION |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BIOTRANSFORMATION |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 690 | 1 | 0 | |a DEACYLATION |
| 690 | 1 | 0 | |a DRUG SOLUBILITY |
| 690 | 1 | 0 | |a DRUG STABILITY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 700 | 1 | |a Iglesias, L.E. | |
| 700 | 1 | |a Iribarren, A.M. | |
| 773 | 0 | |d 2007 |g v. 47 |h pp. 86-90 |k n. 1-2 |p J. Mol. Catal. B Enzym. |x 13811177 |w (AR-BaUEN)CENRE-5687 |t Journal of Molecular Catalysis B: Enzymatic | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.molcatb.2007.04.005 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_13811177_v47_n1-2_p86_Zinni |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v47_n1-2_p86_Zinni |y Registro en la Biblioteca Digital |
| 961 | |a paper_13811177_v47_n1-2_p86_Zinni |b paper |c PE | ||
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| 999 | |c 83606 | ||