Production of L-phenylacetylcarbinol (L-PAC) from benzaldehyde using partially purified pyruvate decarboxylase (PDC)

Biotechnology and Bioengineering

Volumn 49, Issue 1, 1996, Pages 52-62

  Shin, Hyoun S ^a   Rogers, Peter L ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

benzaldehyde; biotransformation; Candida utilis; L phenylacetylcarbinol; pyruvate decarboxylase

Indexed keywords

1 HYDROXY 1 PHENYL 2 PROPANONE; BENZALDEHYDE; METHANOL DERIVATIVE; PYRUVATE DECARBOXYLASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA UTILIS; DRUG PROTEIN BINDING; DRUG TRANSFORMATION; ENZYME ACTIVITY; MOLECULAR INTERACTION; NONHUMAN;

BENZALDEHYDE; CANDIDA UTILIS; L-EPHEDRINE; L-PHENYLACETYLCARBINOL; MOLAR RATIO; PULSE FEEDING; PYRUVATE DECARBOXYLASE;

ALCOHOLS; ALDEHYDES; BYPRODUCTS; DRUG PRODUCTS; ENZYMES; FERMENTATION; FUNGI; GLUCOSE; METABOLISM; PH; PURIFICATION; TEMPERATURE;

BIOCONVERSION;

CANDIDA; FUNGI; PICHIA JADINII;

EID: 0029669427     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19960105)49:1<52::AID-BIT7>3.0.CO;2-S     Document Type: Article

References (29)

1. Astrup, A., Breum, L., Toubro, S., Hein, P., Quaade, F. 1992. The effect and safety of an ephedrine-caffeine compound compared to ephedrine, caffeine and placebo in obese subjects on an energy restricted diet: A double blind trial. Int. J. Obesity 16: 269-277.
2. Astrup, A., Buemann, B., Christensen, N. J., et al. 1992. The effect of ephedrine/caffein mixture in energy expenditure and body composition in obese women. Metabolism 41: 686-688.
3. Bergmeyer, H. U., Grassl, M., Walter, H. E. 1983. Alcohol dehydrogenase from yeast. pp. 139-141 In: H. U. Bergmeyer (ed.), Methods of enzymatic Analysis, 3rd, edition. Vol. II. VCH, Weinheim.
4. Boiteux, A., Hess, B. 1970. Allosteric properties of yeast pyruvate decarboxylase. FEBS Lett. 9: 293-296.
5. Bradford, M. M. 1970. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing, the principle of protein-dye binding. Anal. Biochem. 72: 248-254.
6. Bringer-Meyer, S. Sahm, H. 1988. Acetoin and phenylacetylcarbinol formation by the pyruvate decarboxylase of Zymomonas mobilis and Saccharomyces carlsbergensis. Biocatalysis 1: 321-331.
7. Bringer-Meyer, S., Schimz, K. L., Sahm, H. 1986. Pyruvate decarboxylase from Zymomonas mobilis. Isolation and partial characterization. Arch. Microbiol. 146: 105-110.
8. Crosby, J., Stone, R., Lienhard, G. E. 1970. Mechanisms of thiamine-catalysed reactions, decarboxylation of 2-(1)-carboxyl-1-hydroxyethyl-3,4-dimethylthiazolium chloride. J. Am. Chem. Soc. 92: 2891-2900.
9. Čulič, J., Netrval, J., Ulbrecht, S., Souhrada, J., Vojtišek, V., Vodnansky, M. 1984. Method of the cost reduction in the production of D-(-)-1-phenyl-1-hydroxy-2-propanone for the preparation of L-(-)ephedrine. Czech Patent 222,941 (CI. C07C 49/24).
10. Godfrey, N. B. 1972. Solvent selection via miscibility number. Chemtech 2: 359-363.
11. Gounaris, A. D., Turkenkopf, I., Buckwald, S., Young, A. 1971. Pyruvate decarboxylase: 1. Protein dissociation into subunits under conditions in which thiaminepyrophosphate is released. J. Biol. Chem. 246: 1302-1309.
12. Gruber, M , Wassenaar, J. S. 1960. Inhibition of yeast carboxylase by acetaldehyde. Biochim. Biophys. Acta 38: 355-357.
13. Hopmann, R. F. W 1980 Hydroxyl-ion-induced subunit dissociation of yeast cytoplasmic pyruvate decarboxylase. A circular dichroism study. Eur. J. Biochem. 110: 311-318.
14. Jencks, W. P. 1975. Binding energies, specificity and enzymatic catalysis: The Circe effect. pp. 250-251 In: A. Meister (ed.), Advances in enzymology and related areas of molecular biology, Vol. 43. Wiley, New York.
15. Juni, E. 1961. Evidence for a two site mechanism for decarboxylation of α-keto acid by α-carboxylase. J. Biol. Chem. 236: 2302-2308.
16. Lehmann, H., Fischer, G., Hübner, G., Kohnert, K. D., Schellen-berger, A. 1973. The influence of steric and electronic parameters on the substrate behaviour of α-oxo acids to yeast pyruvate decarboxylase. Eur. J. Biochem. 32: 83-87.
17. Long, A., Ward, O. P. 1989. Biotransformation of aromatic aldehydes by Saccharomyces cerevisiae: Investigation of reaction rates. J. Ind. Microbiol. 4: 49-53.
18. Long, A., Ward, O. P. 1989. Biotransformation of benzaldehyde by Saccharomyces cerevisiae. Characterization of the fermentation and toxicity effects of substrates and products. Biotechnol. Bioeng. 33: 933-941.
19. Mahmoud, W. M., El-Sayed, A. M. M., Coughlin, R. W. 1990. Production of L-phenylacetytcarbinol by immobilized yeast cells: I. Batch Fermentation. Biotechnol. Bioeng. 36: 47-54.
20. Mahmoud, W. M. El-Sayed, A. M. M., Coughlin, R. W. 1990. Production of L-phenylacetylcarbinol by immobilized yeast cells: II. Semicontinuous Fermentation. Biotechnol. Bioeng. 36: 55-63.
21. Nikolova, P., Ward, O. P. 1991. Production of L-phenylacetylcarbinol by biotransformation: Product and by-product formation and activation of the key enzymes in wild-type and ADH isoenzyme mutants of Saccharomyces cerevisiae. Biotechnol. Bioeng. 38: 493-498
22. Perry, R. H. 1984. Perry's chemical engineering handbook, 6th ed. McGraw-Hill International Editions, Chemical Engineering Series, pp. 3-27. New York.
23. Scopes, R. K. 1989. Effect of ethanol on glycolytic enzymes. pp. 89-100 In. N. van Unden (ed.), Alcohol toxicity in yeast and bacteria. CRC Press Inc., Boca Raton, FL.
24. Ullrich, J. 1985. Thiamine pyrophosphate. pp. 457-467 In: H. U. Bergmeyer (ed.), Methods of enzymatic analysis, 3rd ed, Vol. VII. VCH, Weinheim.
25. Ullrich, J., Donner, I. 1970. Fluorimetric study of 2-p-toluidinonaphthalene-6-sulphonate binding to cytoplasmic yeast pyruvate decarboxylase. Hoppe-Seyler's Z. Physiol. Chem. 351: 1030-1034.
26. Urk, H., Schipper, D., Breedveld G. J., Paul, R. M., Scheffers, W. A., van Dijken, J. P. 1989. Localization and kinetics of pyruvate-metabolizing enzymes in relation to aerobic alcohol fermentation in Saccharomyces cerevisiae CBS 8066 and Candida utilis CBS 621. Biochim. Biophys. Acta 992: 78-86.
27. Vojtisek, V., Netrval, J. 1982 Effect of pyruvate decarboxylase activity and pyruvate concentration on the production of L-hydroxy-1-phenylpropanone in Saccharomyces carlsbergensis. Folia Microbiol. 27: 173-177.
28. Westerfeld, W W. 1945. A colorimetric determination of blood acetoin. J. Biol Chem 161. 495-502.
29. Zehender, H., Trescher, D., Ullrich, J. 1987. Improved purification of pyruvate decarboxylase from wheat germ. Its partial characterization and comparison with the yeast enzyme. Eur. J. Biochem. 167. 149-154.