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Abstract:

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.

Registro:

Documento: Artículo
Título:An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one
Autor:Monsalve, L.N.; Machado Rada, M.Y.; Ghini, A.A.; Baldessari, A.
Filiación:Laboratorio de Biocatálisis, Departamento de Quimica Orgánica, UMYMFOR, C1428EGA Buenos Aires, Argentina
Departamento de Quimica Orgánica, UMYMFOR, Facultad de Ciencias Exactas y Naturales, C1428EGA Buenos Aires, Argentina
Palabras clave:20-Pregnane succinates; Candida antarctica lipase B; Enzymatic stereoselective transesterification; 20 pregnane succinate derivative; 20beta hemisuccinyloxy 5alphah pregnan 3 one; hydroxyl group; pregnane derivative; steroid; succinic acid derivative; triacylglycerol lipase; unclassified drug; article; catalysis; chemical structure; enzyme isolation; priority journal; synthesis; transesterification; Candida antarctica
Año:2008
Volumen:64
Número:8
Página de inicio:1721
Página de fin:1730
DOI: http://dx.doi.org/10.1016/j.tet.2007.12.006
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v64_n8_p1721_Monsalve

Referencias:

  • Joe, I., Ramirez, V.D., (2001) Steroids, 66, pp. 529-538
  • 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
  • Grunwell, J.F., Benson, H.D., Johnston, J.O., Petrow, V., (1976) Steroids, 27, pp. 759-771
  • Erlanger, F.B., Borek, F., Beiser, S.M., Lieberman, S., (1959) J. Biol. Chem., 234, pp. 1090-1094
  • Uscheva, A.A., Stankov, B.M., Zachariev, S.G., Marinova, C.P., Kanchev, L.N., (1986) J. Steroid Biochem., 24, pp. 699-702
  • Melgert, B.N., Olinga, P., Jack, V.K., Molema, G., Meijer, D.K.F., Poelstra, K., (2000) J. Hepatol., 32, pp. 603-611
  • McLeod, A.D., Friend, D.R., Tozer, T.N., (1993) Int. J. Pharm., 92, pp. 105-111
  • Ding, W., Qi, X., Li, P., Maitani, Y., Nagai, T., (2005) Int. J. Pharm., 300, pp. 38-47
  • Kuwada, M., Sugano, S., Maki, J., (2001) J. Biochem. Biophys. Methods, 49, pp. 417-431
  • Prakash, B.S., Meyer, H.H.D., Schallenberger, E., van Der Wiel, D.F.M., (1987) J. Steroid Biochem., 28, pp. 623-627
  • 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
  • Kim, J.K., Adam, A., Loo, J.C.K., Ong, H., (1995) J. Pharm. Biomed. Anal., 13, pp. 885-891
  • Feng, W., Graumann, K., Hahn, R., Jungbauer, A., (1999) J. Chromatogr., A, 852, pp. 161-173
  • Mehvar, R., (2000) J. Chromatogr., B: Biomed. Sci. Appl., 744, pp. 293-298
  • Foroutan, S.M., Watson, D.G., (1997) Int. J. Pharm., 157, pp. 103-111
  • Patel, S.B., Khatkatay, I., Desai, M.P., Betrabet, S.S., Toddywalla, V.S., (1994) J. Steroid Biochem. Mol. Biol., 48, pp. 293-296
  • Rosemblit, C., Pozzi, A.G., Ceballos, N.R., (2006) J. Comp. Physiol. B, 176, pp. 559-566
  • Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis, Fundamentals and Applications, , Wiley-VCH, Weinheim pp 1-18
  • Buchholz, K., Kasche, V., Bornscheuer, U.T., (2005) Biocatalysis and Enzyme Technology, , Wiley-VCH, Weinheim pp 109-170
  • Saha, B.C., Demirjian, D.C., (2000) Applied Biocatalysis in Specialty Chemicals and Pharmaceuticals, , ACS, Washington DC pp 263-273
  • García Junceda, E., García-García, J.F., Bastida, A., Fernandez-Mayoralas, A., (2004) Bioorg. Med. Chem., 12, pp. 1817-1834
  • Koeller, K.M., Wong, C.H., (2001) Nature, 409, pp. 232-240
  • Gotor, V., (2002) Org. Process Res. Dev., 6, pp. 420-426
  • Garcia-Urdiales, E., Alfonso, I., Gotor, V., (2005) Chem. Rev., 105, pp. 313-354
  • Ferrero, M., Gotor, V., (2000) Stereoselective Biocatalysis, pp. 579-631. , Patel R.M. (Ed), Marcel Dekker, New York, NY
  • Cruz Silva, M.M., Riva, S., Sá e Melo, M.L., (2005) Tetrahedron, 61, pp. 3065-3073
  • Secundo, F., Carrea, G., De Amici, M., Joppolo di Ventimiglia, S., Dordick, J.S., (2003) Biotechnol. Bioeng., 81, pp. 391-396
  • Cruz Silva, M.M., Sá e Melo, M.M., Parolin, M., Tessaro, D., Riva, S., Danieli, B., (2004) Tetrahedron: Asymmetry, 15, pp. 1173-1179
  • Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedron Lett., 36, pp. 4349-4352
  • Baldessari, A., Bruttomeso, A.C., Gros, E.G., (1996) Helv. Chim. Acta, 79, pp. 999-1004
  • Brutomesso, A.C., Baldessari, A., (2004) J. Mol. Catal. B: Enzym., 29, pp. 149-153
  • Brutomesso, A.C., Tiscornia, A., Baldessari, A., (2004) Biocatal. Biotransf., 22, pp. 215-220
  • Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A., (2005) ARKIVOC, xii, pp. 175-180
  • Ottolina, G., Carrea, G., Riva, S., (1991) Biocatalysis, 5, pp. 131-136
  • Monsalve, L.N., Rosselli, S., Bruno, M., Baldessari, A., (2005) Eur. J. Org. Chem., pp. 2106-2115
  • Rustoy, E.M., Baldessari, A., (2005) Eur. J. Org. Chem., pp. 4628-4632
  • Nakamura, K., Kinoshita, M., Ohno, A., (1995) Tetrahedron, 32, pp. 8799-8808
  • Bommarius, A.S., Riebel, B.R., Biocatalysis in Non-conventional Media (2004) Biocatalysis, Fundamentals and Applications, , Wiley-VCH, Weinheim Chapter 12, pp 347-354
  • Carrea, G., Riva, S., (2000) Angew. Chem., Int. Ed., 39, pp. 2227-2254
  • Persson, M., Costes, D., Wehtje, E., Adlercreutz, P., (2002) Enzyme Microb. Technol., 30, pp. 916-923
  • Giacometti, J., Giacometti, F., (2006) Chem. Biochem. Eng. Q., 20, pp. 269-274
  • Turner, R.B., Voitle, D.M., (1951) J. Am. Chem. Soc., 73, pp. 2283-2286
  • Laane, C., Boeren, S., Vos, K., Veeger, C., (1987) Biotechnol. Bioeng., 30, pp. 81-87
  • Solares, L.F., Lavandera, I., Gotor-Fernandez, V., Brieva, R., Gotor, V., (2006) Tetrahedron, 62, pp. 3284-3291
  • Baldessari, A., Mangone, C.P., Gros, E.G., (2001) J. Mol. Catal. B: Enzym., 11, pp. 335-341
  • Eduardo, S.L., Ghini, A.A., Burton, G., (2003) ARKIVOC, pp. 468-476
  • Joselevich, M., Ghini, A.A., Burton, G., (2003) Org. Biomol. Chem., 1, pp. 939-943
  • Hill, R.A., Kirk, D.N., Makin, H.L.J., Murphy, G.M., (1991) Dictionary of Steroids, , Chapman and Hall, Cambridge p 735
  • Zemlicka, J., Beranek, J., Smrt, J., (1962) Collect. Czech. Chem. Commun., 27, pp. 2784-2795
  • Salomón, C.J., Mata, E.G., Mascaretti, O.A., (1994) J. Org. Chem., 59, pp. 7259-7266
  • Uppenberg, J., Hansen, M.T., Patkar, S., Jones, T.A., (1994) Structure, 2, pp. 293-308
  • Pleiss, J., Fischer, M., Schmid, R.D., (1998) Chem. Phys. Lipids, 93, pp. 67-80
  • Humphrey, W., Dalke, A., Schulten, K., (1996) J. Mol. Graphics, 14, pp. 33-36
  • Nicoletti, D., Ghini, A.A., Burton, G., (1998) An. Asoc. Quim. Argent, 86, pp. 336-341

Citas:

---------- APA ----------
Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A. & Baldessari, A. (2008) . An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one. Tetrahedron, 64(8), 1721-1730.
http://dx.doi.org/10.1016/j.tet.2007.12.006
---------- CHICAGO ----------
Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A., Baldessari, A. "An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one" . Tetrahedron 64, no. 8 (2008) : 1721-1730.
http://dx.doi.org/10.1016/j.tet.2007.12.006
---------- MLA ----------
Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A., Baldessari, A. "An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one" . Tetrahedron, vol. 64, no. 8, 2008, pp. 1721-1730.
http://dx.doi.org/10.1016/j.tet.2007.12.006
---------- VANCOUVER ----------
Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A., Baldessari, A. An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one. Tetrahedron. 2008;64(8):1721-1730.
http://dx.doi.org/10.1016/j.tet.2007.12.006