Enantio-complementary deracemization of (±)-2-hydroxy-4- phenylbutanoic acid and (±)-3-phenyllactic acid using lipase-catalyzed kinetic resolution combined with biocatalytic racemization

Tetrahedron

Volumn 62, Issue 12, 2006, Pages 2912-2916

  Larissegger Schnell, Barbara ^a   Glueck, Silvia M ^b   Kroutil, Wolfgang ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b RESEARCH CENTRE APPLIED BIOCATALYSIS   (Austria)

Author keywords

Biocatalysis; Biocatalytic racemization; Deracemization; Enantio complementary; Lipase

Indexed keywords

2 HYDROXY 4 PHENYLBUTANOIC ACID; 3 PHENYLLACTIC ACID; ATROLACTIC ACID; BUTYRIC ACID; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; KINETICS; LACTOBACILLUS PARACASEI; NONHUMAN; PRIORITY JOURNAL; RACEMIZATION; STEREOISOMERISM;

LACTOBACILLUS PARACASEI;

EID: 32844456411     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.007     Document Type: Article

References (51)

1. K. Ström, J. Sjögren, A. Broberg, and J. Schnürer Appl. Environ. Microbiol. 68 2002 4322 4327
2. V. Dieuleveux, D. van der Pyl, J. Chataud, and M. Gueguen Appl. Environ. Microbiol. 64 1998 800 803
3. N. Valls, M. Lopez-Canet, M. Vallribera, and J. Bonjoch Chem. Eur. J. 7 2001 3446 3460
4. N. Valls, M. Vallribera, S. Carmeli, and J. Bonjoch Org. Lett. 5 2003 447 450
5. K. Ishida, Y. Okita, H. Matsuda, T. Okino, and M. Murakami Tetrahedron 55 1999 10971 10988
6. N. Valls, M. Vallribera, M. Lopez-Canet, and J. Bonjoch J. Org. Chem. 67 2002 4945 4950
7. J. Tao, and K. McGee Org. Process Res. Dev. 6 2002 520 527
8. P.S. Dragovich, T.J. Prins, R. Zhou, E.L. Brown, F.C. Maldonado, S.A. Fuhrman, L.S. Zalman, T. Tuntland, C.A. Lee, A.K. Patick, D.A. Matthews, T.F. Hendrickson, M.B. Kosa, B. Liu, M.R. Batugo, J.-P.R. Gleeson, S.K. Sakata, L. Chen, M.C. Guzman, J.W. Meador, R.A. Ferre, and S.T. Worland J. Med. Chem. 45 2002 1607 1623
9. T. Storz, P. Dittmar, P.F. Fauquex, P. Marschal, W.U. Lottenbach, and H. Steiner Org. Process Res. Dev. 7 2003 559 570
10. W. Adam, M. Lazarus, A. Schmerder, H.-U. Humpf, C.R. Saha-Möller, and P. Schreier Eur. J. Org. Chem. 1998 2013 2018
11. F.J. Aladro, F.M. Guerra, F.J. Moreno-Dorado, J.M. Bustamante, Z.D. Jorge, and G.M. Massanet Tetrahedron Lett. 41 2000 3209 3213
12. R.A. Sheldon Chirotechnology 1993 Marcel Dekker New York pp 362-367
13. R.A. Sheldon, H.J.M. Zeegers, J.P.M. Houbiers, and L.A. Hulshof Chimica Oggi 9 1991 35 47
14. M.R. Attwood, C.H. Hassall, A. Kröhn, G. Lawton, and S. Redshaw J. Chem. Soc., Perkin Trans. 1 1986 1011 1019
15. A. Liese, U. Kragl, H. Kierkels, and B. Schulze Enzyme Microb. Technol. 30 2002 673 681
16. P. Kalaritis, R.W. Regenye, J.J. Partridge, and D.L. Coffen J. Org. Chem. 55 1990 812 815
17. A. Chadha, and M. Manohar Tetrahedron: Asymmetry 6 1995 651 652
18. I. Osprian, M.H. Fechter, and H. Griengl J. Mol. Catal. B: Enzym. 24 2003 89 98
19. S.H. Huang, and S.W. Tsai J. Mol. Catal. B: Enzym. 28 2004 65 69
20. T. Sugai, and H. Ohta Agric. Biol. Chem. 55 1991 293 294
21. F. Spindler, U. Pittelkow, and H.U. Blaser Chirality 3 1991 370 375
22. C.-Y. Chang, and T.-K. Yang Tetrahedron: Asymmetry 14 2003 2239 2245
23. A. Chadha, M. Manohar, T. Soundararajan, and T.S. Lokeswari Tetrahedron: Asymmetry 7 1996 1571 1572
24. N.W. Fadnavis, and K.R. Radhika Tetrahedron: Asymmetry 15 2004 3443 3447
25. E. Schmidt, H.U. Blaser, P.F. Fauquex, G. Sedelmeier, and F. Spindler S. Servi Microbial Reagents in Organic Synthesis NATO ASI Series C Vol. 381 1992 Kluwer Academic Dordrecht 377 388
26. H.U. Blaser, and H.P. Jalett Stud. Surf. Sci. Catal. 78 1993 139 146
27. W. Hummel, H. Schütte, E. Schmidt, C. Wandrey, and M.R. Kula Appl. Microbiol. Biotechnol. 26 1987 409 416
28. D.H. Dao, Y. Kawai, K. Hida, S. Hornes, K. Nakamura, A. Ohno, M. Okamura, and T. Akasaka Bull. Chem. Soc. Jpn. 71 1998 425 432
29. I. Kaluzna, A.A. Andrew, M. Bonilla, M.R. Martzen, and J.D. Stewart J. Mol. Catal. B: Enzym. 17 2002 101 105
30. M.H. Fechter, and H. Griengl K. Drauz H. Waldmann 2nd ed. Enzyme Catalysis in Organic Synthesis Vol. 2 2002 Wiley-VCH Weinheim 974 989
31. M. North Tetrahedron: Asymmetry 14 2003 147 176
32. Y.-F. Wang, S.-T. Chen, K.K.-C. Liu, and C.-H. Wong Tetrahedron Lett. 30 1989 1917 1920
33. P. Herold, A.F. Indolese, M. Studer, H.P. Jalett, U. Siegrist, and H.U. Blaser Tetrahedron 56 2000 6497 6499
34. K. Faber Chem. Eur. J. 7 2001 5004 5010
35. U.T. Strauss, U. Felfer, and K. Faber Tetrahedron: Asymmetry 10 1999 107 117
36. F.F. Huerta, Y.R.S. Laxmi, and J.-E. Bäckvall Org. Lett. 2 2000 1037 1040
37. A. Chadha, and B. Baskar Tetrahedron: Asymmetry 13 2002 1461 1464
38. Although a remarkable number of stereochemically matching pairs of biocatalysts possessing opposite enantio-preference have been reported, the search, for example, 'anti-Kazlauskas' carboxyl ester hydrolases and 'anti-Prelog' alcohol dehydrogenases still represents a major challenge in biocatalysis.
39. U.T. Strauss, and K. Faber Tetrahedron: Asymmetry 10 1999 4079 4081
40. For a review on enzyme-catalyzed racemization see: B. Schnell, K. Faber, and W. Kroutil Adv. Synth. Catal. 345 2003 653 666
41. B. Larissegger-Schnell, W. Kroutil, and K. Faber Synlett 2005 1936 1938
42. For a review on mandelate racemase and its substrate spectrum see: U. Felfer, M. Goriup, M.F. Koegl, U. Wagner, B. Larissegger-Schnell, K. Faber, and W. Kroutil Adv. Synth. Catal. 347 2005 951 961
43. S.M. Glueck, B. Larissegger-Schnell, K. Csar, W. Kroutil, and K. Faber Chem. Commun. 2005 1904 1905
44. S.M. Glueck, M. Pirker, B.M. Nestl, B.T. Ueberbacher, B. Larissegger-Schnell, K. Csar, B. Hauer, R. Stuermer, W. Kroutil, and K. Faber J. Org. Chem. 70 2005 4028 4032
45. 2 and the corresponding carbaldehydes (phenylacetaldehyde/3-phenylpropionaldehyde. See: I.K. Feil, H.-P. Lerch, and D. Schomburg Eur. J. Biochem. 223 1994 857 863
46. W. Hummel, H. Schütte, and M.-R. Kula Appl. Microbiol. Biotechnol. 21 1985 7 15
47. Z. Vuralhan, M.A. Morais, S.-L. Tai, M.D.W. Piper, and J.T. Pronk Appl. Environ. Microbiol. 69 2003 4534 4551
48. O.P. Ward, and A. Singh Curr. Opin. Biotechnol. 11 2000 520 526
49. J.A. Killian, M.D. Van Cleve, Y.F. Shayo, and S.M. Hecht J. Am. Chem. Soc. 120 1998 3032 3042
50. S.G. Cohen, and S.Y. Weinstein J. Am. Chem. Soc. 86 1964 5326 5330
51. A. Chadha, and M. Manohar Tetrahedron: Asymmetry 6 1995 651 652