Deracemization of (±)-mandelic acid using a lipase-mandelate racemase two-enzyme system

Tetrahedron Asymmetry

Volumn 10, Issue 21, 1999, Pages 4079-4081

  Strauss, Ulrike T ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

MANDELATE RACEMASE; MANDELIC ACID; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0033408470     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00436-X     Document Type: Article

References (13)

1. Strauss, U. T.; Felfer, U.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 107-110.
2. For typical examples, see: Xie, Y.-C.; Liu, H.-Z.; Chen, J.-Y. Biotechnol. Lett. 1998, 20, 455-458; Kamphuis, J.; Boesten, W. H. J.; Kaptein, B.; Hermes, H. F. M.; Sonke, T.; Broxterman, Q. B.; van den Tweel, W. J. J.; Schoemaker, H. E. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: New York, 1992; pp. 187-208.
3. For typical examples, see: Xie, Y.-C.; Liu, H.-Z.; Chen, J.-Y. Biotechnol. Lett. 1998, 20, 455-458; Kamphuis, J.; Boesten, W. H. J.; Kaptein, B.; Hermes, H. F. M.; Sonke, T.; Broxterman, Q. B.; van den Tweel, W. J. J.; Schoemaker, H. E. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: New York, 1992; pp. 187-208.
4. It should be kept in mind that the materials to be separated for racemization will be combined at the end of the process.
5. Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417-9476.
6. Racemases belong to the class of isomerases [EC 5.X.X.X].
7. (±)-Mandelic acid (1 g) was dissolved in diisopropyl ether (30 mL) containing vinyl acetate (13.2 mL), lipase Amano P (1 g) was added and the mixture was shaken at 150 rpm at rt for 8-12 h. When the reaction came to a standstill at 50% conversion, the enzyme was recovered by filtration and the solvent was evaporated. See: Jeromin, G. J.; Albertz, M. J. Prakt. Chem. 1992, 334, 526-528.
8. Mandelate racemase [EC 5.1.2.2] is a remarkably stable, cofactor-independent enzyme. For its purification and characterization, see: Hegeman, G. D.; Rosenberg, E. Y.; Kenyon, G. L. Biochemistry 1970, 9, 4029-4035; for a review, see: Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178-186.
9. Mandelate racemase [EC 5.1.2.2] is a remarkably stable, cofactor-independent enzyme. For its purification and characterization, see: Hegeman, G. D.; Rosenberg, E. Y.; Kenyon, G. L. Biochemistry 1970, 9, 4029-4035; for a review, see: Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178-186.
10. 6 U from a 10 L fermentation volume) through enzyme induction. Stecher, H.; Felfer, U.; Faber, K. J. Biotechnol. 1997, 56, 33-40. The enzyme accepts a wide variety of α-hydroxy-η-(hetero)aromatic and α-hydroxy-β,γ-unsaturated carboxylic acids. Felfer, U.; Goriup, M.; Strauss, R. V. A.; Orru, U. T.; Faber, K., unpublished results.
11. 6 U from a 10 L fermentation volume) through enzyme induction. Stecher, H.; Felfer, U.; Faber, K. J. Biotechnol. 1997, 56, 33-40. The enzyme accepts a wide variety of α-hydroxy-η-(hetero)aromatic and α-hydroxy-β,γ-unsaturated carboxylic acids. Felfer, U.; Goriup, M.; Strauss, R. V. A.; Orru, U. T.; Faber, K., unpublished results.
12. 2 (10 mmol), semipurified mandelate racemase (100 mg) immobilized onto DEAE-cellulose (1 g) was added and the mixture was shaken at 150 rpm at rt for 8-12 h. After filtration of the enzyme, the mixture was lyophilized, acidified (3 M HCl, 1 mL) and extracted into diisopropyl ether. The latter solution was subjected to the subsequent resolution step.
13. The remainder to 100% accounts for losses during final recovery. The simultaneous action of lipase and mandelate racemase, which would lead to a dynamic kinetic resolution, is not feasible due to the complete inactivity of mandelate racemase in organic solvents. Strauss, U. T.; Felfer, U., unpublished results.