Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
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2004
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 05129caa a22009017a 4500 | ||
|---|---|---|---|
| 001 | PAPER-4527 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203405.0 | ||
| 008 | 190411s2004 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-2442481817 | |
| 024 | 7 | |2 cas |a carbon, 7440-44-0; prasterone, 53-43-0; triacylglycerol lipase, 9001-62-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCEF | ||
| 100 | 1 | |a Bruttomesso, A.C. | |
| 245 | 1 | 0 | |a Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution |
| 260 | |c 2004 | ||
| 270 | 1 | 0 | |m Baldessari, A.; Depto. de Quim. Organ. and UMYMFOR, Fac. de Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Bovara, R., Canzi, E., Carrea, G., Pilotti, A., Riva, S., (1993) J. Org. Chem., 58, p. 499 | ||
| 504 | |a Riva, S., Bovara, R., Ottolina, G., Carrea, G., (1989) J. Org. Chem., 54, p. 3161 | ||
| 504 | |a Bertinotti, A., Carrea, G., Ottolina, G., Riva, S., (1994) Tetrahedron, 50, p. 13165 | ||
| 504 | |a Danieli, B., Lesma, G., Luiseti, M., Riva, S., (1997) Tetrahedron, 53, p. 5855 | ||
| 504 | |a Oshida, J., Okamoto, M., Azuma, S., (1999) Tetrahedr. Asymm., 10, p. 2337 | ||
| 504 | |a Ferraboschi, P., Colombo, D., Reza-Elahi, S., (2002) Tetrahedr. Asymm., 13, p. 2583 | ||
| 504 | |a Riva, S., (1991) Applied Biocatalysis, 1, p. 179. , H.W. Blanch, D.S. Clark (Eds.), Marcel Dekker, New York Chapter 5 | ||
| 504 | |a Ferrero, M., Gotor, V., (2000) Stereoselective Biocatalysis, p. 579. , R.N. Patel (Ed.), Marcel Dekker, New York Chapter 20 | ||
| 504 | |a Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedr. Lett., 36, p. 4349 | ||
| 504 | |a Baldessari, A., Bruttomesso, A.C., Gros, E.G., (1996) Helv. Chim. Acta, 79, p. 999 | ||
| 504 | |a Tuomi, W.V., Kazlauskas, R.J., (1999) J. Org. Chem., 64, p. 2638 | ||
| 520 | 3 | |a A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective behaviour towards the removal of the 3β- or 16α/16β-acetyl group. The results of the enzymatic deacetylation of pregnanes and androstanes substituted by various groups containing an sp2-hybridised C-atom in ring D could suggest that CAL B activity seems to be conditioned by the occurrence of a polar carbon double bond in this part of the steroid skeleton. Ten new steroid derivatives were obtained through this approach. © 2004 Elsevier B.V. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: We thank UBA and ANPCyT for partial financial support. The authors gratefully acknowledge M.M. Rivero for her assistance in GC analysis. | ||
| 593 | |a Depto. de Quim. Organ. and UMYMFOR, Fac. de Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANDROSTANE |
| 690 | 1 | 0 | |a LIPASE-CATALYSED DEACETYLATION |
| 690 | 1 | 0 | |a PREGNANE |
| 690 | 1 | 0 | |a ACETYLATION |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a DERIVATIVES |
| 690 | 1 | 0 | |a ORGANIC SOLVENTS |
| 690 | 1 | 0 | |a SUBSTITUTION REACTIONS |
| 690 | 1 | 0 | |a ANDROSTANE |
| 690 | 1 | 0 | |a PREGNANE |
| 690 | 1 | 0 | |a ENZYMES |
| 690 | 1 | 0 | |a ACETIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a BACTERIAL ENZYME |
| 690 | 1 | 0 | |a ORGANIC SOLVENT |
| 690 | 1 | 0 | |a PRASTERONE |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a STEROID |
| 690 | 1 | 0 | |a TRIACYLGLYCEROL LIPASE |
| 690 | 1 | 0 | |a ATOM |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 690 | 1 | 0 | |a CANDIDA RUGOSA |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CHEMICAL BOND |
| 690 | 1 | 0 | |a CONFERENCE PAPER |
| 690 | 1 | 0 | |a DEACETYLATION |
| 690 | 1 | 0 | |a HYBRIDIZATION |
| 690 | 1 | 0 | |a MICROORGANISM |
| 690 | 1 | 0 | |a PSEUDOMONAS |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a CANDIDA |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 690 | 1 | 0 | |a CANDIDA RUGOSA |
| 690 | 1 | 0 | |a PSEUDOMONAS |
| 690 | 1 | 0 | |a PSEUDOMONAS SP. |
| 650 | 1 | 7 | |2 spines |a CARBON |
| 650 | 1 | 7 | |2 spines |a CARBON |
| 700 | 1 | |a Baldessari, A. | |
| 773 | 0 | |d 2004 |g v. 29 |h pp. 149-153 |k n. 1-6 |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.2003.10.011 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso |y Registro en la Biblioteca Digital |
| 961 | |a paper_13811177_v29_n1-6_p149_Bruttomesso |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 65480 | ||