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Abstract:

Lipase from Candida cylindracea and Candida antarctica catalyzes the removal of acetyl groups from 3β-acetoxypregn-5-en-20-one and 3β-acetoxy-20-(S)-hydroxycholest-5-en-23-one through a transesterification reaction in organic solvents. © 1995.

Registro:

Documento: Artículo
Título:Enzymatic deacetylation of steroids bearing labile functions
Autor:Baldessari, A.; Maier, M.S.; Gros, E.G.
Filiación:Departamento de Química Orgánica. Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:cholest 5 en 20 ol 23 one; pregnenolone; steroid; triacylglycerol lipase; unclassified drug; article; candida; deacetylation; enzyme activity; reaction analysis; Candida; Candida antarctica; Candida cylindracea
Año:1995
Volumen:36
Número:25
Página de inicio:4349
Página de fin:4352
DOI: http://dx.doi.org/10.1016/0040-4039(95)00791-A
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v36_n25_p4349_Baldessari

Referencias:

  • Greene, Wuts, (1991) Protective Groups in Organic Synthesis, pp. 90-92. , John Wiley and Sons Press, New York
  • Hill, Sharpless, Exon, Regenye, (1985) Organic Synthesis, p. 66
  • Jones, (1986) Tetrahedron, 42, p. 3403. , and references therein
  • Klibanov, (1986) CHEMTECH, p. 354
  • Baldessari, Iglesias, Gros, (1992) J. Chem. Res. (S), p. 204
  • Baldessari, Iglesias, Gros, (1993) J. Chem. Res. (S), p. 382
  • Baldessari, Iglesias, Gros, (1994) Biotechnol. Lett., 16, p. 479
  • Perez, M. G.; Maier M. S. Tetrahedron Lett. in press; Gubicza, Kelemen-Horvath, (1993) J. Mol. Catal., 84, p. L27
  • Laane, Tramper, Lilly, (1987) Biocatalysis in organic media, p. 65. , Elsevier, Amsterdam
  • Nakamura, Takebe, Kitayama, Ohno, (1991) Tetrahedron Lett., 32, p. 4941
  • O'Hagan, Zaidi, (1993) J. Chem. Soc., Perkin Trans. 1, p. 947
  • Uppenberger, Hansen, Patkar, Jones, (1994) Structure, 2, p. 293
  • Lipase (9000–10000 units/ mg substrate) was added to a solution of the steroid ester (10–100 mg) in the indicated solvent (10 mg/ml) and the alcohol (5 mole equiv.) The suspension was shaken on an orbital shaker, 200 rpm at 30°C and the progress of the reaction was monitored by GLC. The reaction was finished by filtration of the enzyme and the products were isolated by flash chromatography on silica gel; 3β,20(S)-dihydroxycholest-5-en-23-one (4): 1H-NMR: (py-d5) δ 0.94 (d, 6H, J: 6.5 Hz, H-26 and H-27), 1.11 (s, 6H, H-18 and H-19), 1.66 (s, 3H, H-21), 3.90 (bs, 1H, H-3α), 5.45 (bs, 1H, H-6). 13C-NMR: (py-d5) 216.0 (C-23), 141.9 (C-5), 121.1 (C-6), 73.9 (C-20), 71.2 (C-3), 59.5 (C-17), 57.2 (C-14), 55.0 (C-22), 54.0 (C-24), 50.4 (C-9), 43.4 (C-4), 43.0 (C-13), 40.4 (C-12), 37.8 (C-1), 36.8 (C-10), 32.5 (C-2), 32.0 (C-7), 31.6 (C-8), 27.3 (C-21), 24.3 (C-25), 24.1 (C-16), 23.1 (C-15), 22.6 (C-26)∗, 22.5 (C-27)∗, 21.2 (C-11), 19.5 (C-19), 13.7 (C-18). MS: m/z (%) 316 (M+ - 101, 3β-acetoxypregn-5-en-20-one by retroaldolic reaction on 4, 9.5), 298 (12), 283 (7)

Citas:

---------- APA ----------
Baldessari, A., Maier, M.S. & Gros, E.G. (1995) . Enzymatic deacetylation of steroids bearing labile functions. Tetrahedron Letters, 36(25), 4349-4352.
http://dx.doi.org/10.1016/0040-4039(95)00791-A
---------- CHICAGO ----------
Baldessari, A., Maier, M.S., Gros, E.G. "Enzymatic deacetylation of steroids bearing labile functions" . Tetrahedron Letters 36, no. 25 (1995) : 4349-4352.
http://dx.doi.org/10.1016/0040-4039(95)00791-A
---------- MLA ----------
Baldessari, A., Maier, M.S., Gros, E.G. "Enzymatic deacetylation of steroids bearing labile functions" . Tetrahedron Letters, vol. 36, no. 25, 1995, pp. 4349-4352.
http://dx.doi.org/10.1016/0040-4039(95)00791-A
---------- VANCOUVER ----------
Baldessari, A., Maier, M.S., Gros, E.G. Enzymatic deacetylation of steroids bearing labile functions. Tetrahedron Lett. 1995;36(25):4349-4352.
http://dx.doi.org/10.1016/0040-4039(95)00791-A