Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno de la institución.
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells. © 2004 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
Autor:Rustoy, E.M.; Pereyra, E.N.; Moreno, S.; Baldessari, A.
Filiación:Depto. de Quim. Organ. Y UMYMFOR, Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Pabellon 2, P., Argentina
Depto. de Quím. Biol., Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Pabellon 2, P., Argentina
Palabras clave:2 oxoglutaric acid; ester derivative; fungal enzyme; lactone derivative; triacylglycerol lipase; acidification; alkylation; article; biocatalyst; catalysis; derivatization; drug synthesis; enantiomer; enzyme mechanism; esterification; lactonization; priority journal
Año:2004
Volumen:15
Número:23
Página de inicio:3763
Página de fin:3768
DOI: http://dx.doi.org/10.1016/j.tetasy.2004.10.013
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:2 oxoglutaric acid, 328-50-7; triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v15_n23_p3763_Rustoy

Referencias:

  • Garciía, C., Martin, T., Martin, V.S., (2001) J. Org. Chem., 66, pp. 1420-1428
  • Xu, M.-H., Wang, W., Xia, L.-J., Lin, G.-Q., (2001) J. Org. Chem., 66, pp. 3953-3962
  • Mulzer, J., (1995) Comprehensive Organic Functional Group Transformations, 5, pp. 121-179. , Elsevier Oxford
  • Fukui, H., Tuschiya, Y., Fujita, K., Nakawaga, T., Koshino, H., Nakata, T., (1997) Bioorg. Med. Chem. Lett., 7, pp. 2081-2086
  • Murta, M.M., De Azevedo, M.B.M., Greene, A.E., (1993) J. Org. Chem., 58, pp. 7537-7541
  • Sibi, M.P., Liu, P., Ji, J., Hajra, S., Chen, J., (2002) J. Org. Chem., 67, pp. 1738-1745
  • Sledski, A.W., Boukouvalas, J., (1989) Stud. Nat. Prod. Chem., 3, pp. 157-171. , Elsevier Amsterdam
  • Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis, Fundamentals and Applications, , Wiley-VCH Weinheim
  • Carrea, G., Riva, S., (2000) Angew. Chem., Int. Ed., 39, pp. 2226-2254
  • Csuk, R., Glanzer, B., (1991) Chem. Rev., 91, pp. 49-97
  • Patel, R.N., (1999) Stereoselective Biocatalysis, , Marcel Dekker Amsterdam
  • Gutman, A.L., Bravdo, T., (1989) J. Org. Chem., 54, pp. 4263-4265
  • Brenna, E., Dei Negri, C., Fuganti, C., Serra, S., (2001) Tetrahedron: Asymmetry, 12, pp. 1871-1879
  • Drioli, S., Nitti, P., Pittaco, G., Tossut, L., Valentin, E., (1999) Tetrahedron: Asymmetry, 10, pp. 2713-2728
  • Baldessari, A., Mangone, C.P., (2001) J. Mol. Catal. B: Enzym., 11, pp. 335-341
  • Mangone, C.P., Pereyra, E.N., Argimon, S., Moreno, S., Baldessari, A., (2002) Enzyme Microb. Technol., 30, pp. 596-601
  • Baldessari, A., Gros, E.G., Argentine Patent AR 002219B1; Bruttomesso, A.C., Tiscornia, A., Baldessari, A., (2004) Biocatal. Biotransform., 22, pp. 215-220
  • Baldessari, A., Mangone, C.P., (2002) Biocatal. Biotransform., 20, pp. 275-279
  • Rottahus, O., Kruger, D., Demuth, M., Schaffer, K., (1997) Tetrahedron, 53, pp. 935-938
  • Nakamura, K., Kondo, S., Kawai, Y., Ohno, A., (1993) Bull. Chem. Soc. Jpn., 66, pp. 2738-2743
  • Nakamura, K., Kondo, S., Kawai, Y., Ohno, A., (1991) Tetrahedron Lett., 32, pp. 7075-7078
  • Hoffmann, M., Wasielewski, C., (1975) Rocz. Chem., 49, pp. 151-158
  • Hachihama, Y., Shono, T.J., (1955) Chem. Soc. Jpn., 58, pp. 806-812
  • Cappon, J.J., Baart, J., Van Del Walle, G.A.M., Rapp, J., Lugtenburg, J., (1991) Recl. Trav. Chim. Pays-Bas, 110, pp. 158-166
  • Hartman, F.C., Barker, R.J., (1964) J. Org. Chem., 29, pp. 873-877
  • Ravid, U., Silverstein, R., Smith, L.R., (1978) Tetrahedron, 34, pp. 1449-1452
  • Dao, D.H., Okamura, M., Akasaka, T., Kawai, Y., Hida, K., Ohno, A., (1998) Tetrahedron: Asymmetry, pp. 2725-2737
  • Kebs, H.A., Eggleston, L.V., (1943) Biochem. J., 37, pp. 335-338

Citas:

---------- APA ----------
Rustoy, E.M., Pereyra, E.N., Moreno, S. & Baldessari, A. (2004) . Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid. Tetrahedron Asymmetry, 15(23), 3763-3768.
http://dx.doi.org/10.1016/j.tetasy.2004.10.013
---------- CHICAGO ----------
Rustoy, E.M., Pereyra, E.N., Moreno, S., Baldessari, A. "Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid" . Tetrahedron Asymmetry 15, no. 23 (2004) : 3763-3768.
http://dx.doi.org/10.1016/j.tetasy.2004.10.013
---------- MLA ----------
Rustoy, E.M., Pereyra, E.N., Moreno, S., Baldessari, A. "Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid" . Tetrahedron Asymmetry, vol. 15, no. 23, 2004, pp. 3763-3768.
http://dx.doi.org/10.1016/j.tetasy.2004.10.013
---------- VANCOUVER ----------
Rustoy, E.M., Pereyra, E.N., Moreno, S., Baldessari, A. Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid. Tetrahedron Asymmetry. 2004;15(23):3763-3768.
http://dx.doi.org/10.1016/j.tetasy.2004.10.013