An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one
Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only t...
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2008
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| LEADER | 09765caa a22012737a 4500 | ||
|---|---|---|---|
| 001 | PAPER-6085 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203545.0 | ||
| 008 | 190411s2008 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-38349018729 | |
| 024 | 7 | |2 cas |a triacylglycerol lipase, 9001-62-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TETRA | ||
| 100 | 1 | |a Monsalve, L.N. | |
| 245 | 1 | 3 | |a An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| 260 | |c 2008 | ||
| 270 | 1 | 0 | |m Baldessari, A.; Laboratorio de Biocatálisis, Departamento de Quimica Orgánica, UMYMFOR, C1428EGA Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Joe, I., Ramirez, V.D., (2001) Steroids, 66, pp. 529-538 | ||
| 504 | |a Everts, M., Kok, R.J., Asgeirsdottir, S.A., Melgert, B.N., Moolenaar, T.J.M., Koning, G.A., van Luyn, M.J.A., Molema, G., (2002) J. Immunol., 168, pp. 883-889 | ||
| 504 | |a Grunwell, J.F., Benson, H.D., Johnston, J.O., Petrow, V., (1976) Steroids, 27, pp. 759-771 | ||
| 504 | |a Erlanger, F.B., Borek, F., Beiser, S.M., Lieberman, S., (1959) J. Biol. Chem., 234, pp. 1090-1094 | ||
| 504 | |a Uscheva, A.A., Stankov, B.M., Zachariev, S.G., Marinova, C.P., Kanchev, L.N., (1986) J. Steroid Biochem., 24, pp. 699-702 | ||
| 504 | |a Melgert, B.N., Olinga, P., Jack, V.K., Molema, G., Meijer, D.K.F., Poelstra, K., (2000) J. Hepatol., 32, pp. 603-611 | ||
| 504 | |a McLeod, A.D., Friend, D.R., Tozer, T.N., (1993) Int. J. Pharm., 92, pp. 105-111 | ||
| 504 | |a Ding, W., Qi, X., Li, P., Maitani, Y., Nagai, T., (2005) Int. J. Pharm., 300, pp. 38-47 | ||
| 504 | |a Kuwada, M., Sugano, S., Maki, J., (2001) J. Biochem. Biophys. Methods, 49, pp. 417-431 | ||
| 504 | |a Prakash, B.S., Meyer, H.H.D., Schallenberger, E., van Der Wiel, D.F.M., (1987) J. Steroid Biochem., 28, pp. 623-627 | ||
| 504 | |a Arevalo, J.H., Hassig, C.A., Stura, E.A., Sims, M.J., Taussig, M.J., Wilson, I.A., (1994) J. Mol. Biol., 241, pp. 663-690 | ||
| 504 | |a Kim, J.K., Adam, A., Loo, J.C.K., Ong, H., (1995) J. Pharm. Biomed. Anal., 13, pp. 885-891 | ||
| 504 | |a Feng, W., Graumann, K., Hahn, R., Jungbauer, A., (1999) J. Chromatogr., A, 852, pp. 161-173 | ||
| 504 | |a Mehvar, R., (2000) J. Chromatogr., B: Biomed. Sci. Appl., 744, pp. 293-298 | ||
| 504 | |a Foroutan, S.M., Watson, D.G., (1997) Int. J. Pharm., 157, pp. 103-111 | ||
| 504 | |a Patel, S.B., Khatkatay, I., Desai, M.P., Betrabet, S.S., Toddywalla, V.S., (1994) J. Steroid Biochem. Mol. Biol., 48, pp. 293-296 | ||
| 504 | |a Rosemblit, C., Pozzi, A.G., Ceballos, N.R., (2006) J. Comp. Physiol. B, 176, pp. 559-566 | ||
| 504 | |a Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis, Fundamentals and Applications, , Wiley-VCH, Weinheim pp 1-18 | ||
| 504 | |a Buchholz, K., Kasche, V., Bornscheuer, U.T., (2005) Biocatalysis and Enzyme Technology, , Wiley-VCH, Weinheim pp 109-170 | ||
| 504 | |a Saha, B.C., Demirjian, D.C., (2000) Applied Biocatalysis in Specialty Chemicals and Pharmaceuticals, , ACS, Washington DC pp 263-273 | ||
| 504 | |a García Junceda, E., García-García, J.F., Bastida, A., Fernandez-Mayoralas, A., (2004) Bioorg. Med. Chem., 12, pp. 1817-1834 | ||
| 504 | |a Koeller, K.M., Wong, C.H., (2001) Nature, 409, pp. 232-240 | ||
| 504 | |a Gotor, V., (2002) Org. Process Res. Dev., 6, pp. 420-426 | ||
| 504 | |a Garcia-Urdiales, E., Alfonso, I., Gotor, V., (2005) Chem. Rev., 105, pp. 313-354 | ||
| 504 | |a Ferrero, M., Gotor, V., (2000) Stereoselective Biocatalysis, pp. 579-631. , Patel R.M. (Ed), Marcel Dekker, New York, NY | ||
| 504 | |a Cruz Silva, M.M., Riva, S., Sá e Melo, M.L., (2005) Tetrahedron, 61, pp. 3065-3073 | ||
| 504 | |a Secundo, F., Carrea, G., De Amici, M., Joppolo di Ventimiglia, S., Dordick, J.S., (2003) Biotechnol. Bioeng., 81, pp. 391-396 | ||
| 504 | |a Cruz Silva, M.M., Sá e Melo, M.M., Parolin, M., Tessaro, D., Riva, S., Danieli, B., (2004) Tetrahedron: Asymmetry, 15, pp. 1173-1179 | ||
| 504 | |a Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedron Lett., 36, pp. 4349-4352 | ||
| 504 | |a Baldessari, A., Bruttomeso, A.C., Gros, E.G., (1996) Helv. Chim. Acta, 79, pp. 999-1004 | ||
| 504 | |a Brutomesso, A.C., Baldessari, A., (2004) J. Mol. Catal. B: Enzym., 29, pp. 149-153 | ||
| 504 | |a Brutomesso, A.C., Tiscornia, A., Baldessari, A., (2004) Biocatal. Biotransf., 22, pp. 215-220 | ||
| 504 | |a Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A., (2005) ARKIVOC, xii, pp. 175-180 | ||
| 504 | |a Ottolina, G., Carrea, G., Riva, S., (1991) Biocatalysis, 5, pp. 131-136 | ||
| 504 | |a Monsalve, L.N., Rosselli, S., Bruno, M., Baldessari, A., (2005) Eur. J. Org. Chem., pp. 2106-2115 | ||
| 504 | |a Rustoy, E.M., Baldessari, A., (2005) Eur. J. Org. Chem., pp. 4628-4632 | ||
| 504 | |a Nakamura, K., Kinoshita, M., Ohno, A., (1995) Tetrahedron, 32, pp. 8799-8808 | ||
| 504 | |a Bommarius, A.S., Riebel, B.R., Biocatalysis in Non-conventional Media (2004) Biocatalysis, Fundamentals and Applications, , Wiley-VCH, Weinheim Chapter 12, pp 347-354 | ||
| 504 | |a Carrea, G., Riva, S., (2000) Angew. Chem., Int. Ed., 39, pp. 2227-2254 | ||
| 504 | |a Persson, M., Costes, D., Wehtje, E., Adlercreutz, P., (2002) Enzyme Microb. Technol., 30, pp. 916-923 | ||
| 504 | |a Giacometti, J., Giacometti, F., (2006) Chem. Biochem. Eng. Q., 20, pp. 269-274 | ||
| 504 | |a Turner, R.B., Voitle, D.M., (1951) J. Am. Chem. Soc., 73, pp. 2283-2286 | ||
| 504 | |a Laane, C., Boeren, S., Vos, K., Veeger, C., (1987) Biotechnol. Bioeng., 30, pp. 81-87 | ||
| 504 | |a Solares, L.F., Lavandera, I., Gotor-Fernandez, V., Brieva, R., Gotor, V., (2006) Tetrahedron, 62, pp. 3284-3291 | ||
| 504 | |a Baldessari, A., Mangone, C.P., Gros, E.G., (2001) J. Mol. Catal. B: Enzym., 11, pp. 335-341 | ||
| 504 | |a Eduardo, S.L., Ghini, A.A., Burton, G., (2003) ARKIVOC, pp. 468-476 | ||
| 504 | |a Joselevich, M., Ghini, A.A., Burton, G., (2003) Org. Biomol. Chem., 1, pp. 939-943 | ||
| 504 | |a Hill, R.A., Kirk, D.N., Makin, H.L.J., Murphy, G.M., (1991) Dictionary of Steroids, , Chapman and Hall, Cambridge p 735 | ||
| 504 | |a Zemlicka, J., Beranek, J., Smrt, J., (1962) Collect. Czech. Chem. Commun., 27, pp. 2784-2795 | ||
| 504 | |a Salomón, C.J., Mata, E.G., Mascaretti, O.A., (1994) J. Org. Chem., 59, pp. 7259-7266 | ||
| 504 | |a Uppenberg, J., Hansen, M.T., Patkar, S., Jones, T.A., (1994) Structure, 2, pp. 293-308 | ||
| 504 | |a Pleiss, J., Fischer, M., Schmid, R.D., (1998) Chem. Phys. Lipids, 93, pp. 67-80 | ||
| 504 | |a Humphrey, W., Dalke, A., Schulten, K., (1996) J. Mol. Graphics, 14, pp. 33-36 | ||
| 504 | |a Nicoletti, D., Ghini, A.A., Burton, G., (1998) An. Asoc. Quim. Argent, 86, pp. 336-341 | ||
| 520 | 3 | |a Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only the 20β-succinyloxy derivatives are obtained. These compounds are obtained in variable yield, depending on the substitution in the ring A. The enzymatic approach allowed, for the first time, the synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one, novel compound useful as a precursor of steroid-protein conjugates. © 2007 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Umweltbundesamt, X089 | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 2005, 32735 | ||
| 536 | |a Detalles de la financiación: We thank Dr. Ernesto Mata for the generous gift of bis(tributyltin)oxide. A.B. thanks UBA (X089) and ANPCyT (PICT 2005, 32735) for partial financial support. A.B. and A.A.G. are Research Members of CONICET. | ||
| 593 | |a Laboratorio de Biocatálisis, Departamento de Quimica Orgánica, UMYMFOR, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Departamento de Quimica Orgánica, UMYMFOR, Facultad de Ciencias Exactas y Naturales, C1428EGA Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 20-PREGNANE SUCCINATES |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA LIPASE B |
| 690 | 1 | 0 | |a ENZYMATIC STEREOSELECTIVE TRANSESTERIFICATION |
| 690 | 1 | 0 | |a 20 PREGNANE SUCCINATE DERIVATIVE |
| 690 | 1 | 0 | |a 20BETA HEMISUCCINYLOXY 5ALPHAH PREGNAN 3 ONE |
| 690 | 1 | 0 | |a HYDROXYL GROUP |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a STEROID |
| 690 | 1 | 0 | |a SUCCINIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a TRIACYLGLYCEROL LIPASE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a ENZYME ISOLATION |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a TRANSESTERIFICATION |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 700 | 1 | |a Machado Rada, M.Y. | |
| 700 | 1 | |a Ghini, A.A. | |
| 700 | 1 | |a Baldessari, A. | |
| 773 | 0 | |d 2008 |g v. 64 |h pp. 1721-1730 |k n. 8 |p Tetrahedron |x 00404020 |w (AR-BaUEN)CENRE-45 |t Tetrahedron | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.tet.2007.12.006 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404020_v64_n8_p1721_Monsalve |y Handle |
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