Enzymatic resolution of analgesics: δ-Hydroxytramadol, ε-hydroxytramadol and O-desmethyltramadol

Tetrahedron Asymmetry

Volumn 11, Issue 4, 2000, Pages 917-928

  Gais, Hans Joachim ^a   Griebel, Carsten ^a   Buschmann, Helmut ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b GRÜNENTHAL GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYTRAMADOL; 6 HYDROXYTRAMADOL; ANALGESIC AGENT; FUNCTIONAL GROUP; FUNGAL ENZYME; LIVER ENZYME; O DESMETHYLTRAMADOL; TRAMADOL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA RUGOSA; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SWINE;

EID: 0034629444     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00008-2     Document Type: Article

References (52)

1. Cancer Pain Relief; WHO: Geneva. 1986.
2. Ventafridda, V.; Tamburini, M.; Caraceni, A.; de Conno, F.; Naldi, F. Cancer 1987, 59, 851.
3. Casey, A. F.; Parfitt, R. T. Opioid Analgesics; Plenum Press: New York, 1986.
4. Zens, M.; Jurna, I. Lehrbuch der Schmerztherapie; Wissenschaftl. Verlagsgesellschaft: Stuttgart, 1993.
5. Williams, M.; Kowaluk, E. A.; Arneric, P. J. Med. Chem. 1999, 42, 1481.
6. Mutschler, E. Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie; Wissenschaftl. Verlagsgesellschaft: Stuttgart, 1996.
7. Flohé, L.; Friderichs, E. Arz.-Forsch. (Drug Res. II) 1978, 28, 99.
8. Frankus, V. E.; Friderichs, E.; Kim, S.; Osterloh, G. Arz.-Forsch. (Drug Res. II) 1978, 28, 114.
9. Raffa, R. B.; Friderichs, E.; Reimann, W.; Shank, R. P.; Codd, E. E.; Vaught, J. L.; Jacoby, H. I.; Selve, N. J. Pharmacol. Exp. Ther. 1993, 267, 331.
10. Lintz, W.; Erlaçin, S.; Frankus, E.; Uragg, H. Arz.-Forsch. (Drug Res. II) 1981, 1, 1932.
11. Graudums, I.; Winter, W.; Frankus, E. DE 19547766A1, 20.12.1995; Chem. Abstr. 1997, 127, 121560 g.
12. Buschmann, H.; Strassburger, W.; Norma, S.; Friderichs, E. EP 0753506B1, 22.6.1996; Chem. Abstr. 1997, 126, 171384 c.
13. 11,12.
14. For reviews, see: (a) Gais, H.-J. Hydrolysis and Formation of C-O-Bonds in Enzyme Catalysis in Organic Synthesis; Drauz, K.; Waldmann, H., Eds.; VCH: Weinheim, 1995; Vol. I, p. 165.
15. (b) Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis; Wiley-VCH: Weinheim, 1999.
16. (c) Roberts, S. M. Biocatalysts for Fine Chemical Synthesis; Wiley: Chichester, 1999.
17. For some pertinent examples, see: (a) Esser, P.; Buschmann, H.; Meyer-Stork, M.; Scharf, H.-D. Angew. Chem. 1992, 104, 1254; Angew. Chem., Int. Ed. Engl. 1992, 31, 1190.
18. For some pertinent examples, see: (a) Esser, P.; Buschmann, H.; Meyer-Stork, M.; Scharf, H.-D. Angew. Chem. 1992, 104, 1254; Angew. Chem., Int. Ed. Engl. 1992, 31, 1190.
19. (b) Commins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
20. (c) Stead, P.; Marley, H.; Mahmoudian, M.; Webb, G.; Noble, D.; Ip, Y. T.; Piga, E.; Rossi, T.; Roberts, S. M.; Dawson, M. J. Tetrahedron: Asymmetry 1996, 7, 2247.
21. (d) Fukazawa, T.; Shimoji, Y.; Hashimoto, T. Tetrahedron: Asymmetry 1996, 7, 1649.
22. (e) Carpenter, B. E.; Hunt, I. R.; Keay, B. A. Tetrahedron: Asymmetry 1996, 7, 3107.
23. (f) Barz, M.; Herdtweck, E.; Thiel, W. R. Tetrahedron: Asymmetry 1996, 7, 1717.
24. (g) Crotti, P.; Di Bussolo, V.; Favero, L.; Minutolo, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 1347.
25. (h) Noheda, P.; Garciá, G.; Pozuelo, M. C.; Herredón, B. Tetrahedron: Asymmetry 1996, 7, 2801.
26. (i) Sakagami, H.; Samiza, K.; Kamibubo, T.; Ogasawara, K. Synlett 1996, 163.
27. (j) Maestro, A.; Astorga, C.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3153.
28. (k) Forró, E.; Fülöp, F. Tetrahedron: Asymmetry 1999, 10, 1985.
29. (l) Sarakinos, G.; Corey, E. J. Org. Lett. 1999, 1, 1741.
30. PLE consists of different isoenzyme fractions (Ref. 14a), and PLE-Chirazyme E-1 is an enriched isoenzyme mixture.
31. For all enzymatic resolutions described in this paper the yields given are based on one enantiomer.
32. For a definition of the E value, see: Chen, C.-S.; Sih, C. J. Angew. Chem. 1989, 101, 711; Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
33. For a definition of the E value, see: Chen, C.-S.; Sih, C. J. Angew. Chem. 1989, 101, 711; Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
34. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
35. Riefling, B. F.; Brümmer, W. K.; Gais, H.-J. NATO ASI Series C, 1986, 178, 347.
36. Gais, H.-J.; Hemmerle, H.; Kossek, S. Synthesis 1992, 169.
37. Kita, Y.; Takebe, Y.; Murata, K.; Naka, T.; Akai, S. Tetrahedron Lett. 1996, 37, 7369.
38. Weber, H. K.; Zuegg, J.; Faber, K.; Pleiss, J.
39. Grünenthal GmbH, unpublished results.
40. Ruppert, S.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 3657.
41. Jungen, M.; Gais, H.-J. Tetrahedron: Asymmetry 1999, 10, 3747.
42. Alcohol rac-7 was prepared by demethylation of rac-2 with diisobutylaluminum hydride: Buschmann, H.; Jansen, P.; Winter, W.; Strassburger, W.; Graudums, I.; Friderich, E. DE 19601744, 14.12.95; Chem. Abstr. 1997, 127, 190 519.
43. Hesse, M. Alkaloide; Wiley-VCH: Weinheim, 1999.
44. Fujimoto, Y.; Iwadate, N.; Ikekawa, N. J. Chem. Soc., Chem. Commun. 1985, 1333.
45. Wu, S.-H.; Zhang, L.-Q.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. Tetrahedron Lett. 1985, 26, 4323.
46. Inagaki, M.; Hiratake, J.; Nisioka, T.; Oda, J. Agric. Biol. Chem. 1989, 7, 1879.
47. Kazlauskas, R. J. J. Am. Chem. Soc. 1989, 111, 4953.
48. Hoshino, O.; Tanahashi, R.; Okada, M.; Akita, H.; Oishi, T. Tetrahedron: Asymmetry 1993, 4, 933.
49. Hoshino, O.; Fuchino, H.; Kikuchi, M. Heterocycles 1994, 39, 553.
50. Hennies, H. H.; Friderichs, E.; Schneider, J. Arz.-Forsch. (Drug Res. II) 1988, 7, 877.
51. Elsing, B.; Blaschke, G. J. Chromatogr. Biomed. Appl. 1993, 2, 223.
52. Driessen, B.; Reimann, W.; Giertz, H. Br. J. Pharmacol. 1993, 3, 806.