Enzymatic laboratory scale production of homochiral (R)-3-fluorolactic acid methyl ester via enantiospecific reduction of sodium fluoropyruvate catalyzed by rabbit muscle L-lactate dehydrogenase (L-LDH)

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1237-1240

  Goncalves L P B ^a   Antunes, O A C ^a   Pinto, G F ^a   Oestreicher, E G ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

3 FLUOROLACTIC ACID METHYL ESTER; ALCOHOL DEHYDROGENASE; LACTATE DEHYDROGENASE; LACTIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; HORSE; LIVER; MUSCLE; NONHUMAN; PRIORITY JOURNAL; RABBIT; REACTION ANALYSIS;

EID: 0029895345     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00131-0     Document Type: Article

References (42)

1. a) Jones, J. B. Tetrahedron 1986, 42, 3351-3403;
2. b) Hummel, W. ; Kula, M.-R. Eur. J. Biochem. 1989, 184, 1-13;
3. c) Santaniello, E. ; Ferraboschi, P. ; Grisenti, P. ; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140;
4. d) Faber, K. "Biotransformations in Organic Chemistry", Springer, Berlin, 1992.
5. e) Kvittingen, L. Tetrahedron 1994, 50, 8253-8274;
6. f) Wong, C.-H. ; Whitesides, G. W. "Enzymes in Synthetic Organic Chemistry", Elsevier, Oxford, 1994.
7. g)Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17-51.
8. h) Fang, J-M. ; Lin, C.-H. ; Bradshaw, C. W. ; Wong, C.-H. J. Chem. Soc. Perkin Trans.1 1995, 967-978.
9. Corey, E. J. ; Cheng, X.-M. "The Logic of Chemical Synthesis"; John Wiley and Sons; New York; 1989.
10. Hanessian, S. "Total Synthesis of Natural Products The 'Chiron' Approach", Pergamon Press; Oxford; 1983.
11. a)Harris, H.D. J. Org. Chem. 1963, 28, 745;
12. b) Danilewicz, J.C.; Kemp, J.E.G. J. Med. Chem. 1973, 16,168;
13. c) Fuganti, C.; Grasselli, P.; Seneci, P.F.; Servi, S.; Casati, P. Tetrahedron Lett. 1986, 27, 2061;
14. d) Kan, K.; Miyama, A.; Hamaguchi, S.; Oshashi, T; Watanabe, K. Agric.Biol.Chem. 1985, 49, 207;
15. e) Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855.
16. f) Ader, U.; Schneider, M.P. Tetrahedron: Asymmetry 1992, 3, 201;
17. g) Ader, U.; Schneider, M.P. Tetrahedron: Asymmetry 1992, 3, 205;
18. h) Ader, U.; Schneider, M.P. Tetrahedron: Asymmetry 1992, 3, 521;
19. i) Klunder, J.M.; Ko, S.Y.; Sharpless, K.B. J.Org.Chem. 1986, 51, 3710.
20. Bentley, J. M. ; Wadsworth, H. J. ; Willis, C. L. J. Chem. Soc. Chem. Commun. 1995, 231-232.
21. a) Bernardi, R. ; Bravo, P. ; Cardillo, R. ; Ghiringhelli, D. ; Resnati, G. J. Chem. Soc. Perkin Trans.1 1988, 2831;
22. b) Bernardi, R. ; Bravo, P. ; Cardillo, R. ; Ghiringhelli, D. ; Resnati, G. J. Chem. Soc. Perkin Trans.1 1990, 579.
23. a) Bravo, P. ; Resnati, G. Tetrahedron:Asymmetry 1990, 1, 661-692
24. b) Wong, C.-H. ; Matos, J. R. J. Org. Chem. 1985, 50, 1992.
25. Kim, M.-J. ; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 2959-2964.
26. Hirschbein, B. L. ; Whitesides, G. M. J. Am. Chem. Soc. 1982, 104, 4458-4460.
27. a) Shaked, Z. ; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 7104;
28. b) Jakovak, I. J. ; Goodbrand, H. B. ; Lok, K. P. ; Jones, J. B. J Am. Chem. Soc. 1982, 104, 4659-4665;
29. c) Lee, L. ; Whitesides, G. M. J. Am. Chem. Soc. 1985, 107, 6999-7008;
30. d) Wong, C.-H. Science 1989, 244, 1145-1152;
31. e) Itozawa, T. ; Kise, H. Bull. Chem. Soc. Jpn. 1994, 67, 3304;
32. f) Pereira, D. A. ; Pinto, G. F. ; Oestreicher, E. G. J. Biotechnol. 1994, 34, 43-50.
33. Paiva, L. M. C. ; Pinto, G. F. ; Oestreicher, E. G. Biom. Biochim. Acta 1991, 50, 25-29.
34. 13 . HLADH assays were performed essentially as described in reference 11.
35. Zewe, V., Fromm, H. J. J. Biol. Chem. 1962, 237, 1668-1675.
36. + (grade III-C) and bovine serum albumin (BSA) (Fraction V) were purchased from Sigma Chemical Company. BHMC, Diazald® kit and reagent and ethyl alcohol (spectrophotometric UV grade) were products from Aldrich Chemical Company. All other reagents used were of analytical grade obtained from E. Merck, Darmstadt, Germany.
37. -1 .
38. 0' = -100 cal/ mol (Mahler, H. R. ; Cordes, E. H. "Biological Chemistry", 2nd ed. ,p532, Harper Int. Ed. , New York, 1971.
39. 0' = -100 cal/ mol (Mahler, H. R. ; Cordes, E. H. "Biological Chemistry", 2nd ed. ,p532, Harper Int. Ed. , New York, 1971.
40. 0' = -100 cal/ mol (Mahler, H. R. ; Cordes, E. H. "Biological Chemistry", 2nd ed. ,p532, Harper Int. Ed. , New York, 1971.
41. 10c
42. 25 D= -5 (c=1, EtOH).