Biocatalytic preparation of enantioenriched 3,4-dihydroxypiperidines and theoretical study of Candida antarctica lipase B enantioselectivity

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3284-3291

  Solares, Laura F ^a   Lavandera, Iván ^a   Gotor Fernández, Vicente ^a   Brieva, Rosario ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Camdida antarctica lipase B; Dihydroxypiperidine; Enzymatic hydrolysis and transesterification; Molecular modeling

Indexed keywords

1 BENZYLOXYCARBONYL 1,2,5,6 TETRAHYDROPYRIDINE; 1 BENZYLOXYCARBONYL 3,4 DIHYDROXYCARBONYL 3 HYDROXYPIPERIDINE; 1 BENZYLOXYCARBONYL 3,4 DIHYDROXYPIPERIDINE; 1 BENZYLOXYCARBONYL 3,4 EPOXYPYRIDINE; 3,4 DIACETOXY 1 BENZYLOXYCARBONYL 4 HYDROXYPIPERIDINE; 3,4 DIACETOXY 1 BENZYLOXYCARBONYL PIPERIDINE; 3,4 DIACETOXY 1 BENZYLOXYCARBONYLPIPERIDINE; 3,4 DIHYDROXYPIPERIDINE DERIVETAIVE; FUNGAL ENZYME; LIPASE B; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; DRUG ACETYLATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; PRIORITY JOURNAL;

BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA;

EID: 33644898905     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.061     Document Type: Article

References (51)

1. T.D. Butters, R.A. Dwek, and F.M. Platt Chem. Rev. 100 2000 4683 4696
2. F.-X. Felpin, K. Bouberkeur, and J. Lebrenton J. Org. Chem. 69 2004 1497 1503 and references cited therein
3. P.B. Anzeveno, L.J. Creemer, J.K. Daniel, C.-H.R. King, and P.S. Liu J. Org. Chem. 54 1989 2539 2542
4. J.A. Balfour, and D. McTavish Drugs 46 1993 1025 1054
5. L. Ratner, N.V. Heyden, and D. Dedera Virology 181 1999 180 192 and references cited therein
6. P.E. Gross, M.A. Baker, J.P. Carver, and J.W. Dennis Clin. Cancer Res. 1 1995 935 944
7. Y. Ichikawa, Y. Igasashi, M. Ichikawa, and Y. Suhara J. Am. Chem. Soc. 120 1998 3007 3018
8. S.J. Williams, R. Hoos, and S.G. Withers J. Am. Chem. Soc. 122 2000 2223 2235
9. J. Cossy, J.L. Molina, and J.-R. Desmurs Tetrahedron Lett. 42 2001 5713 5715
10. P.C. Waldmeier, L. Maitre, P.A. Baumann, K. Hauser, S. Bischoff, H. Bittiger, and R. Paioni Eur. J. Pharmacol. 130 1986 1 10
11. D. Chang, M.F. Heringa, B. Witholt, and Z. Li J. Org. Chem. 68 2003 8599 8606
12. D.H.G. Crout, V.S.B. Gaudet, K. Laumen, and M.P. Schneider J. Chem. Soc., Chem. Commun. 1986 808 810
13. Z.-F. Xie, I. Nakamura, H. Suemune, and K. Sakai J. Chem. Soc., Chem. Commun. 1988 966 967
14. R. Seemayer, and M.P. Schneider J. Chem. Soc., Chem. Commun. 1991 49 50
15. G. Caron, and J. Kazlauskas J. Org. Chem. 56 1991 7251 7256
16. S.-H. Yu, and S.-K. Chung Tetrahedron: Asymmetry 2004 581 584
17. L.F. Solares, R. Brieva, M. Quirós, I. Llorente, M. Bayod, and V. Gotor Tetrahedron: Asymmetry 15 2004 341 345
18. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
19. J. García, S. Fernández, M. Ferrero, Y.S. Sanghvi, and V. Gotor Org. Lett. 6 2004 3759 3762
20. J. Uppenberg, S.A. Patkar, T. Bergfors, and T.A. Jones J. Mol. Biol. 235 1994 790 792
21. J. Uppenberg, M.T. Hansen, S.A. Patkar, and T.A. Jones Structure 2 1994 293 298
22. J. Uppenberg, N. Öhrner, M. Norin, K. Hult, G.J. Kleywegt, S. Patkar, V. Waagen, T. Anthonsen, and T.A. Jones Biochemistry 34 1995 16838 16851
23. F. Hæffner, T. Norin, and K. Hult Biophys. J. 74 1998 1251 1262
24. A.D. Cuiper, M.L.C.E. Kouwijzer, P.D.J. Grootenhius, R.M. Kellogg, and B.L. Feringa J. Org. Chem. 64 1999 9529 9537
25. R.T. Otto, H. Scheib, U.T. Bornscheuer, J. Pleiss, C. Syldatk, and R.D. Schmid J. Mol. Catal. B 8 2000 201 211
26. S. Park, E. Forró, H. Grewal, F. Fülöp, and R.J. Kazlauskas Adv. Synth. Catal. 345 2003 986 995
27. T.K. Venkatachalam, P. Samuel, G. Li, S. Qazi, C. Mao, S. Pendergrass, and F.M. Uckun Bioorg. Med. Chem. 12 2004 3371 3381
28. L.M. Levy, I. Lavandera, and V. Gotor Org. Biomol. Chem. 2 2004 2572 2577
29. I. Lavandera, S. Fernández, J. Magdalena, M. Ferrero, R.J. Kazlauskas, and V. Gotor ChemBioChem 6 2005 1381 1390
30. S. Raza, L. Fransson, and K. Hult Protein Sci. 10 2001 329 338
31. J. Ottosson, J.C. Rotticci-Mulder, D. Rotticci, and K. Hult Protein Sci. 10 2001 1769 1774
32. J. Ottosson, L. Fransson, and K. Hult Protein Sci. 11 2002 1462 1471
33. S. Lutz Tetrahedron: Asymmetry 15 2004 2743 2748
34. Recently, an S-selective CAL-B has been designed using a rational redesign approach: A.O. Magnusson, M. Takwa, A. Hamberg, and K. Hult Angew. Chem., Int. Ed. 44 2005 4582 4585
35. A. Magnusson, K. Hult, and M. Holmquist J. Am. Chem. Soc. 123 2001 4354 4355
36. C. Branneby, P. Carlqvist, A. Magnusson, K. Hult, T. Brinck, and P. Berglund J. Am. Chem. Soc. 125 2003 874 875
37. P. Carlqvist, M. Svedendahl, C. Branneby, K. Hult, T. Brinck, and P. Berglund ChemBioChem 6 2005 331 336
38. Wild-type CAL-B has also achieved this type of transformation: O. Torre, I. Alfonso, and V. Gotor Chem. Commun. 2004 1724 1725
39. O. Torre, V. Gotor-Fernández, I. Alfonso, L.F. García-Alles, and V. Gotor Adv. Synth. Catal. 347 2005 1007 1014
40. P. Carlqvist, R. Eklund, K. Hult, and T. Brinck J. Mol. Model. 9 2003 164 171
41. Magnusson et al. have shown that for wild-type CAL-B there is enough space up to an ethyl moiety into the stereospecifity pocket: A.O. Magnusson, J.C. Rotticci-Mulder, A. Santagostino, and K. Hult ChemBioChem 6 2005 1051 1056
42. R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, and L.A. Cuccia J. Org. Chem. 56 1991 2656 2665
43. E. Forró, L.T. Kanerva, and F. Fülöp Tetrahedron: Asymmetry 9 1998 513 520
44. A. Luna, C. Astorga, F. Fülöp, and V. Gotor Tetrahedron: Asymmetry 9 1998 4483 4487
45. C. Brunet, M. Zarevucka, Z. Wimmer, and M.-D. Legoy Enzyme Microb. Technol. 31 2002 609 614
46. L.M. Levy, J.R. Dehli, and V. Gotor Tetrahedron: Asymmetry 14 2003 2053 2058
47. R. Tanikaga, Y. Matsumoto, M. Sakaguchi, Y. Koyama, and K. Ono Tetrahedron Lett. 44 2003 6781 6783
48. W.D. Cornell, P. Cieplak, C.I. Bayley, and P.A. Kollmann J. Am. Chem. Soc. 115 1993 9620 9631
49. S.J. Weiner, P.A. Kollman, D.A. Case, U.C. Singh, C. Ghio, G. Alagona, S. Profeta, and P. Weiner J. Am. Chem. Soc. 106 1984 765 784
50. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stümer, and T. Zelinski Angew. Chem., Int. Ed. 43 2004 788 824
51. DeLano, W. L. The PyMOL Molecular Graphics System; DeLano Scientific LLC: San Carlos, CA, USA 2004; http://www.pymol.org.