Production of ethyl (r)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo-4-phenylbutanoate in an interface bioreactor

Bioscience, Biotechnology and Biochemistry

Volumn 62, Issue 9, 1998, Pages 1762-1767

  Oda, Shinobu ^a   Inada, Yuichi ^a   Kobayashi, Atsuko ^a   Ohta, Hiromichi ^a,b  

^a KANSAI PAINT CO LTD   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Bioconversion; Interface bioreactor; Microbial transformation; Non aqueous bioreactor; Stereoselective reduction

Indexed keywords

2 HYDROXY 4 PHENYLBUTYRIC ACID; 2-HYDROXY-4-PHENYLBUTYRIC ACID; AGAR; ARYLBUTYRIC ACID DERIVATIVE;

ARTICLE; BIOREACTOR; CANDIDA; METABOLISM; OXIDATION REDUCTION REACTION; RHODOTORULA;

AGAR; BIOREACTORS; CANDIDA; OXIDATION-REDUCTION; PHENYLBUTYRATES; RHODOTORULA;

EID: 0032150224     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.1762     Document Type: Article

References (34)

1. Ondetti, M. A. and Cushman, D. W., Inhibition of the renin-an-giotensin system. A new approach to the therapy of hypertension. J. Med. Chem., 24, 355-361 (1981).
2. Maruyama, S., Nakagomi, K., Tomizuka, N., and Suzuki, H., Angiotensin I-converting enzyme inhibitor derived from an enzymatic hydrolysate of casein. II. Isolation and bradykinin-potentiating activity on the ileum of rats. Agric. Biol. Chem., 49, 1405-1409 (1985).
3. Iwasaki, G., Kimura, R., Numao, N., and Kondo, K., A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors. Chem. Pharm. Bull., 37, 280-283 (1989).
4. Yamamoto, K. and Ootsubo, K., Japan Kokai Tokkyo Koho, 192190 (Aug. 3, 1993).
5. Nohira, H., Oonishi, T., Yamamoto, K., and Kumagai, N., Japan Kokai Tokkyo Koho, 204838 (Sep. 6, 1991).
6. Ito, M. and Kobayashi, Y., Japan Kokai Tokkyo Koho, 281098 (Nov. 13, 1989).
7. Miyata, A. and Sato, H., Japan Kokai Tokkyo Koho, 225499 (Sep. 8, 1989).
8. Sugai, T. and Ohta, H., Japan Kokai Tokkyo Koho, 200391 (July 21, 1992).
9. Sugai, T. and Ohta, H., A simple preparation of (R)-2-hydroxy-4-phenylbutanoic acid. Agric. Biol. Chem., 55, 293-294 (1991).
10. Bradshaw, C. W„ Wong, C.-H., Hummel, W., and Kula, M.-R., Enzyme-catalyzed asymmetric synthesis of (S)-2-amino-4-phenylbutanoic acid and (R)-2-hydroxy-4-phenylbutanoic acid. Bioorg. Chem., 19, 29-39 (1991).
11. Nikaido, T., Matsuyama, A., Ito, M., Kobayashi, Y., and Oonishi, H., Stereoselective reduction of 2-oxo-4-phenylbutanoate to (R)-2-hydroxy-4-phenyl-butanoate with microbial cells. Biosci. Biotech. Biochem., 56, 2066-2067 (1992).
12. Dao, D. H., Kawai, Y., Hida, K., Hornes, S., Nakamura, K., Ohno, A., Okamura, M., and Akasaka, T., Stereochemical control in microbial reduction. 30. Reduction of alkyl 2-oxo-4-phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors. Bull. Chem. Soc. Jpn., 71, 425-432 (1998).
13. Oda, S. and Ohta, H., Microbial transformation on interface between hydrophilic carriers and hydrophobic organic solvents. Biosci. Biotech. Biochem., 56, 2041-2045 (1992).
14. Oda, S. and Ohta, H., Interface bioreactor: Bioconversion process on an interface between an organic solvent and a polymer gel. J. Jpn. Soc. Colour Material (in Japanese), 70, 538-546 (1997).
15. Oda, S., Inada, Y., Kato, A., Matsudomi, N., and Ohta, H., Production of (S)-citronellic acid and (i?)-citronellol with an interface bioreactor. J. Ferment. Bioeng., 80, 559-564 (1995).
16. Oda, S., Kato, A., Matsudomi, N., and Ohta, H., Enantioselec-tive oxidation of racemic citronellol with an interface bioreactor. Biosci. Biotech. Biochem., 60, 83-87 (1996).
17. Sugai, T., Katoh, O., and Ohta, H., Chemo-enzymatic synthesis of (R, R)-(—)-pyrenophorin. Tetrahedron, 51, 11987-11998 (1995)
18. Oda, S., Tanaka, J., and Ohta, H., Interface bioreactor packed with synthetic polymer pad: Application to hydrolysis of neat 2-ethylhexyl acetate. J. Ferment. Bioeng., 86, 84-89 (1998).
19. Hegeman, G. D., Synthesis of the enzymes of the mandelate pathway by Pseudomonas putida. J. Bacteriol., 9, 1140-1154 (1966).
20. Vakeria, D., Vivian, A., and Fewson, C. A., Isolation, characterization and mapping of mandelate pathway mutants of Acinetobacter calcoaceticus. J. Gen. Microbiol., 130, 2893-2903 (1984).
21. Oda, S., Kikuchi, Y., and Nanishi, Y., Synthesis of optically active mandelic acid via microbial oxidation of racemic 1-phenyl-1,2-ethanediol. Biosci. Biotech. Biochem., 56, 1216-1220 (1992).
22. Oda, S., Kato, A., Matsudomi, N., and Ohta, H., Production of aliphatic carboxylic acids via microbial oxidation of 1-alkanols with interface bioreactor. J. Ferment. Bioeng., 78, 149-154 (1994).
23. Yadav, B. S., Osumi, K., Amemura, A., and Harada, T., Multiple forms of NAD-dependent alcohol dehydrogenase in Hansen-ula miso IFO 0146 capable of growing on ethanol: Occurrence of an inducible alcohol dehydrogenase. J. Ferment. Technol., 57, 244-247 (1979).
24. Simpfessel, L., Presence and regulation of the synthesis of two alcohol dehydrogenases from Saccharomyces cerevisiae. Biochim. Biophys. Acta, 151, 317-329 (1968).
25. Fowler, P. W., Ball, A. J. S., and Grifiths, D. E., The control of alcohol dehydrogenase isozyme synthesis in Saccharomyces cerevisiae. Can. J. Biochem., 50, 35-43 (1972).
26. Oda, S., Inada, Y., Kobayashi, A., Kato, A., Matsudomi, N., and Ohta, H., Coupling of metabolism and bioconversion: Microbial esterification of citronellol with acetyl coenzyme A produced via metabolism of glucose in an interface bioreactor. Appl. Environ. Microbiol., 62, 2216-2220 (1996).
27. Oda, S. and Ohta, H., Double coupling of acetyl coenzyme A production and microbial esterification with alcohol acetyltransferase in an interface bioreactor. /. Ferment. Bioeng., 83, 423-428 (1997).
28. Oda, S. and Ohta, H., Alleviation of toxicity of poisonous organic compounds on hydrophilic carrier /hydrophobic organic solvent interface. Biosci. Biotech. Biochem., 56, 1515-1517 (1992).
29. Schmidt, E., Ghisalba, O., Gygax, D., and Sedelmeier, G., Optimization of a process for the production of (i?)-2-hydroxy-4-phenylbutyric acid: An intermediate for inhibitors of angiotensin converting enzyme. J. Biotechnol., 24, 315-327 (1992).
30. Kawai, Y., Kondo, S., Tsujimoto, M., Nakamura, K., and Ohno, A., Stereochemical control in microbial reduction. XXIII. Thermal treatment of bakers’ yeast for controlling the stereoselectivity of reductions. Bull. Chem. Soc. Jpn., 67, 2244-2247 (1994).
31. Kawai, Y., Takanobe, K., and Ohno, A., Stereochemical control in microbial reduction. XXV. Additives controlling diastereoselectivity in a microbial reduction of ethyl 2-methyl-3-oxobutanoate. Bull. Chem. Soc. Jpn., 68, 285-288 (1995).
32. Ishihara, K., Higashi, Y., Tsuboi, S., and Utaka, M., Effects of additives in the reduction using bakers’ yeast cell-free extract. Chem. Lett., 1995, 253-254.
33. Nakamura, K., Kawai, Y., Oka, S., and Ohno, A., Stereochemical control in microbial reduction. 8. Stereochemical control in microbial reduction of /5-keto esters. Bull. Chem. Soc. Jpn., 62, 875-879 (1989).
34. Jayasinghe, L. Y., Koditsuwakku, D., Smallridge, A. J., and Trewhella, M. A., The use of organic solvent systems in the yeast mediated reduction of ethyl acetoacetate. Bull. Chem. Soc. Jpn., 67, 2528-2531 (1994).