Enantioselective reduction of pentoxifylline to lisofylline using whole-cell Lactobacillus kefiri biotransformation

Biotechnology Journal

Volumn 2, Issue 4, 2007, Pages 492-496

  Pekala, Elzbieta ^a   Godawska Matysik, Anna ^a   Zelaszczyk, Dorota ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

Alcohol dehydrogenase; Biotransformation; Enantiomeric excess; Lactobacillus kefiri; Lisofylline

Indexed keywords

2 PROPANOL; GLUCOSE; LISOFYLLINE; PENTOXIFYLLINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BIOTRANSFORMATION; CONCENTRATION RESPONSE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LACTOBACILLUS; LACTOBACILLUS KEFIRI; NONHUMAN; POLARIMETRY; PRIORITY JOURNAL; WHOLE CELL;

2-PROPANOL; BIOREACTORS; BIOTRANSFORMATION; CELL CULTURE TECHNIQUES; GLUCOSE; LACTOBACILLUS; OXIDATION-REDUCTION; PENTOXIFYLLINE; STEREOISOMERISM;

LACTOBACILLUS KEFIRI;

EID: 34248393464     PISSN: 18606768     EISSN: None     Source Type: Journal    
DOI: 10.1002/biot.200600236     Document Type: Article

References (37)

1. Nakamura, K., Matsuda, T., Harada, T., Chiral synthesis of secondary alcohols using Geotrichum candidum. Chirality 2002, 14, 703-708.
2. Patel., R. N., Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr. Opin. Biotechnol. 2001, 12, 587-604.
3. Arterburn, J. B., Selective oxidation of secondary alcohols. Tetrahedron 2001, 57, 9765-9788.
4. Kroutil, W., Mang, H., Edegger, K., Faber, K., Recent advances in the biocatalytic reduction of ketones and oxidations of sec-alcohols. Curr. Opin. Chem. Biol. 2004, 8, 120-126.
5. Wandrey, C., Biochemical reaction engineering for redox reactions. Chem. Rec. 2004, 4, 254-256.
6. Kula, M.-T., Dehydrogenases in the synthesis of chiral compounds, in: Patel R. N. (Ed.), Stereoselective Biocatalysis, Dekker, New York 2002, pp. 839-866.
7. Yamada, H., Shimizu, S., Kataoka, M., Sakai, H., Miyoshi, S., A novel NADPH-dependent aldehyde reductase, catalyzing asymmetric reduction of β-keto acid esters, from Sporobolomyces salmonicolor: purification and characterization. FEMS Microbiol. Lett. 1990, 70, 45-48.
8. Kataoka, M., Kita, K., Wada, M., Yosohara, Y. et al., Novel bioreduction system for the production of chiral alcohols. Appl. Microbiol. Biotechnol. 2003, 62, 437-445.
9. Schmid, A., Dordick, J. S., Hauer, B., Kiener, A. et al., Industrial biocatalysis today and tomorrow. Nature 2001, 409, 258-268.
10. Sieh, C. J., Chen, C.-S., Microbial asymmetric catalysis - enatioselective reduction of ketones. Angew. Chem. Int. Ed. Engl. 1984, 23, 570-578.
11. Prelog, V., Specification of the stereospecificity of some oxidoreductases by diamond lattice sections. Pure Appl. Chem. 1984, 9, 119-130.
12. Keinan, E., Seth, K. K., Lamed, R., Synthetic applications of alcoholdehydrogenase from Thermoanaerobium brockii. Ann. N. Y. Acad. Sci. 1987, 501, 130-149.
13. Seebach., D., Zuger., M. F., Giovannini, F., Sonnleitner, B., Fichter, A., Preparative microbial of β-oxoesters with Thermoanaerobium brockii. Angew. Chem. Int. Ed. Engl. 1984, 23, 151-152.
14. Nakamura, K., Yamanaka, R., Matsuda, T., Harada, T., Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asymmetry 2003, 14, 2659-2681.
15. Keinan, E., Hafeli, E. K., Seth, K. K., Lamed, R., Thermostable enzymes in organic synthesis. 2. Asymmetric reduction of ketones with alcohol dehydrogenase. J. Am. Chem. Soc. 1986, 108, 162-169.
16. Hummel, W., Reduction of acetophenone to R(+)-phenylethanol by a new alcohol dehydrogenase from Lactobacillus kefir. Appl. Microbiol. Biotechnol. 1990, 34, 15-19.
17. Bradshaw, C. W., Hummel, W., Wong, C.-H., Lactobacillus kefir alcohol dehydrogenase: a useful catalyst for synthesis. J. Org. Chem. 1992, 57, 1532-1536.
18. Haberland, J., Kriegesmann, A., Wolfram, E., Hummel, W., Liese, A., Diastereoselective synthesis of optically active (2R,5R)-hexanediol. Appl. Microbiol. Biotechnol. 2002, 58, 595-599.
19. Ernst, M., Kaup, B., Muller, M., Bringer-Meyer, S., Sahm, H., Enantioselective reduction of carbonyl compounds by whole-cell biotransformation, combining a formate dehydrogenase and a (R)-specific alcohol dehydrogenase. Appl. Microbiol. Biotechnol. 2005, 66, 629-634.
20. Amidjojo, M., Franco-Lara, E., Nowak, A., Link, H., Weuster-Botz, D., Asymmetric synthesis of tert-butyl (3R,5S)-6-chloro-dihydroxyhexanoate with Lactobacillus kefir. Appl. Microbiol. Biotechnol. 2005, 69, 9-15.
21. Pfruender, H., Amidjojo, M., Hang, F., Weuster-Botz, D., Production of Lactobacillus kefir cells for asymmetric synthesis of a 3,5-dihydroxycarboxylate. Appl. Microbiol. Biotechnol. 2005, 67, 619-622.
22. Amidjojo, A., Weuster-Botz, D., Asymmetric synthesis of the chiral synthon ethyl (S)-4-chloro-3-hydroxybutanoate using Lactobacillus kefir. Tetrahedron: Asymmetry 2005, 16, 899-901.
23. Tan, A. W., Fischbach, M., Huebner, H., Buchholz, R. et al., Synthesis of enantiopure (5R)-hydroxyhexane-2-one with immobilised whole cells of Lactobacillus kefiri. Appl. Microbiol. Biotechnol. 2006, 71, 289-293.
24. Hummel, W., Enzyme-catalyzed synthesis of optically pure R(+)-phenylethanol. Biotechnol. Lett. 1990, 12, 403-408.
25. Gelo-Pujic, M., Le Guayader, F., Schlama, T., Microbial and asymmetric in the reduction of 1-[3,5-bis(trifluoromethylOphenyl]-ethanone. Tetrahedron: Asymmetry 2006, 17, 2000-2005.
26. Weckebecker, A., Hummel W., Cloning, expression, and characterization of an (R)-specific alcohol dehydrogenase from Lactobacillus kefir. Biocat. Biotranf. 2006, 24, 380-389.
27. Strampfer, W., Kosjek, B., Kroutil, W., Faber, K., Recent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols. Curr. Opin. Chem. Biol. 2004, 8, 120-126.
28. van der Donk, W. A., Regeneration of cofactors for use in biocatalysis. Curr. Opin. Biotechnol. 2003, 14, 583-589.
29. Lillibridge, J. A., Kalhorn, T. F., Slattery, J. T., Metabolism of lisofylline and pentoxifylline in human liver microsomes and cytosol. Drug Met. Dispos. 1996, 24, 1174-1179.
30. Abraham, E., Bursten, S., Shenkar, R., Allbee, J. et al., Phosphatidic acid signaling mediates lung cytokine expression and lung inflammatory injury after hemorrhage in mice. J. Exp. Med. 1995, 181, 569-575.
31. Wong, J. S., Ara, S., Keyes, S. R., Herbst, R. et al., Lisofylline as a modifier of radiation therapy. Oncol. Res. 1996, 8, 513-518.
32. Yang, Z., Chen, M., Nadler, J. L, Lisofylline: a potential lead for treatment of diabetes. Biochem. Pharmacol. 2005, 69, 1-5.
33. Bianco, J. A., Woodson, P., Parubek, D., Singer, J., (Cell Therapeut., Inc.) Enantiomeric hydroxylated xanthine cpds. JP 94509584, JP 96259565, WO 9317684.
34. Klein, J. P., Leigh, A. J., Michnick, J., Kumar, A. M., Underiner, G. E., (Cell Therapeut., Inc.) Asymmetric synthesis of chiral secondary alcohols. DE 9531450.
35. Aretz, W., Furrer, H., Gebert, U., Hinze, H.-J., (Hoechst AG) Process for the enantoselective preparation of (ω-1)-hydroxyalkyl xanthines. DE 3942872.
36. Pekala, E., Wójcik, T., Enantioselective biotransformation of pentoxifylline into lisofylline using wine yeast biocatalysis. Acta Polon. Pharmac. Drug Res. in press, 2007.
37. Wyska, E., Pekala, E., Szymura-Oleksiak, J., Interconversion and tissue distribution of pentoxifylline and lisofylline in mice. Chirality 2006, 18, 644-651.