Selectivity of Candida rugosa lipase in simultaneous separation of skeletal isomers, desymmetrization, and kinetic racemate cleavage of 9-oxabicyclononanediols

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2225-2229

  Hegemann, Klaus ^a   Schimanski, Holger ^a   Höweler, Udo ^b   Haufe, Günter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b CHEOPS   (Germany)

Author keywords

Bicyclic diols; Desymmetrization; Enantiospecificity; Lipase catalyzed acetylation; Molecular modeling; Racemate cleavage

Indexed keywords

ALKANEDIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; CANDIDA RUGOSA; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME DEGRADATION; ISOMER; NONHUMAN; RACEMIC MIXTURE; STEREOCHEMISTRY;

CANDIDA; CANDIDA RUGOSA;

EID: 0037416890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02876-9     Document Type: Article

References (44)

1. Kagan H.B., Dang T.P. J. Am. Chem. Soc. 94:1972;6429-6433.
2. Whitesell J.K. Chem. Rev. 89:1989;1581-1590.
3. Alexakis A., Mangeney P. Tetrahedron: Asymmetry. 1:1990;477-511.
4. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley & Sons, New York.
5. Nieman J.A., Keay B.A. Tetrahedron: Asymmetry. 7:1996;3521-3526.
6. Ahrens H., Paetow M., Hoppe D. Tetrahedron Lett. 33:1992;5327-5330.
7. Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobayashi H., Akutagaura S., Ohta T., Takaya H., Noyori R. J. Am. Chem. Soc. 110:1988;629-631.
8. Aldous D.J., Dutton W.M., Steel P.G. Tetrahedron:Asymmetry. 11:2000;2455-2462.
9. Lieser J.K. Synth. Commun. 13:1983;765-767.
10. Fauve A., Veschambre H. Biocatalysis. 3:1990;95-109.
11. Otten S., Fröhlich R., Haufe G. Tetrahedron: Asymmetry. 9:1998;189-191. and references cited therein.
12. Wallace J.S., Baldwin B.W., Morrow C.J. J. Org. Chem. 57:1992;5231-5239.
13. Mattson A., Öhrner N., Hult K., Norin T. Tetrahedron: Asymmetry. 4:1993;925-930.
14. Mattson A., Orrenius C., Öhrner N., Unelius C.R., Hult K., Norin T. Acta Chim. Scand. 50:1996;918-921.
15. Alexandre F.-R., Huet F. Tetrahedron: Asymmetry. 9:1998;2391-2410.
16. Matsumoto K., Sato Y., Shimjo M., Hatanaka M. Tetrahedron:Asymmetry. 11:2000;1965-1973.
17. Gung B.W., Dickson H., Shockley S. Tetrahedron Lett. 42:2001;4761-4763.
18. Guo Z.-W., Wu S.-H., Chen C.-S., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 112:1990;4942-4945.
19. Caron G., Kazlauskas R.J. Tetrahedron: Asymmetry. 5:1994;657-664.
20. Kim M.-J., Lee J.S., Jeong N., Choi Y.K. J. Org. Chem. 58:1993;6483-6485.
21. Hegemann, K. Ph.D. Thesis, Universität Münster, 1997.
22. Grochulski P., Li Y., Schrag J.D., Bouthillier F., Smith P., Harrison D., Rubin B., Cygler M. J. Biol. Chem. 268:1993;12843-12847.
23. Cygler M., Grochulski P., Kazlauskas R.J., Schrag J.D., Bouthilier F., Rubin B., Serregi A.N., Gupta A.K. J. Am. Chem. Soc. 116:1994;3180-3186.
24. For an excellent review on enzyme-catalyzed syntheses in organic solvents, see: Carrea, G.; Riva, S. Angew. Chem. 2000, 112, 2312-2341; Angew. Chem., Int. Ed. 2000, 39, 2226-2254.
25. For an excellent review on enzyme-catalyzed syntheses in organic solvents, see: Carrea, G.; Riva, S. Angew. Chem. 2000, 112, 2312-2341; Angew. Chem., Int. Ed. 2000, 39, 2226-2254.
26. Lafont, P.; Vivant, G. Fr. Pat. 1,336,187, 1963 [Chem. Abstr. 1963, 60, 2803] Frazer, A. H. US Pat. 3,347,826, 1967 [Chem. Abstr. 1968, 68, P2819].
27. Duthaler R.O., Wicker K., Ackermann P., Ganter C. Helv. Chim. Acta. 55:1972;1809-1829.
28. Eaton P.E., Millikan R. Synthesis. 1990;483-484.
29. The determination of the absolute configuration by X-ray crystal structure analysis of these compounds will be reported in detail elsewhere (Hegemann, K.; Fröhlich, R.; Haufe, G., in preparation).
30. 20=-29.3 (c 1, ethyl acetate).
31. Oberhauser T., Faber K., Griengl H. Tetrahedron. 45:1985;1679-1682.
32. Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., Cuccia L.A. J. Org. Chem. 56:1991;2656-2665.
33. Ahmed S.N., Kazlauskas R.J., Morinville A.H., Grochulski P., Schrag J.D., Cygler M. Biocatalysis. 9:1994;209-225.
34. Cahn, R. S.; Ingold, C. K. Prelog, V. Angew. Chem. 1966, 78, 413-447; Angew. Chem., Int. Ed. Engl. 1966, 5, 385-419 Prelog, V.; Helmchen, G. Angew. Chem. 1982, 94, 614-631; Angew. Chem., Int. Ed. Engl. 1982, 21, 567-584.
35. Naemura K., Matsumura T., Komatsu M., Hirose Y., Chikamatsu H. J. Chem. Soc., Chem. Commun. 1988;239-241.
36. Ganter C., Wicker K. Helv. Chim. Acta. 51:1968;1599-1603.
37. Stetter H., Meissner H.J., Last W.D. Chem. Ber. 101:1968;2889-2893.
38. Haufe G. Tetrahedron Lett. 25:1984;4365-4368.
39. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stuart J.J.P. J. Am. Chem. Soc. 107:1985;3902-3909 MOPAC7, AM1, QCPE Program No. 455.
40. 21.
41. Höweler, U. CHEOPS, 1999; the optimization was done using the MaxiMoby 5.2 program.
42. Weiner S.J., Kollman P.A., Case D.A., Singh U.C., Ghio C., Alagona G., Profeta S., Weiner P. J. Am. Chem. Soc. 106:1984;765-784.
43. For the conformational analysis for both enantiomers of 3 (or the enantiotopic OH-groups of 2) the two torsions of the connection between the phosphate group (cf. Ref. 24) and the substituent (O-P-O-C-Sub and P-O-C-Sub-H-Sub) have been varied. Torsions have been run through in 10° steps for 360°. All conformations within 200 kcal/mol compared to the lowest minimum in the subsequent optimization have been taken into account. In this course the phosphate group, the substituent and the side chain of the amino acids of the active site (Glu-208, Ser-209 (bound to the phosphorus), Phe-296, Glu-341, Phe-344, Phe 345, His-449 and Ser-450) could adapt to each other.
44. Tuomi W.V., Kazlauskas R.J. J. Org. Chem. 64:1999;2638-2647.