A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

Tetrahedron Asymmetry

Volumn 21, Issue 20, 2010, Pages 2448-2454

  D'Antona, Nicola ^a   Morrone, Raffaele ^a   Bovicelli, Paolo ^a   Gambera, Giovanni ^a   Kubáč, David ^b   Martínková, Ludmila ^b  

^a CNR   (Italy)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

4,5,6 TRIHYDROXYCYCLOHEX 2 ENECARBONITRILE; AMIDASE; CYCLOHEXENE DERIVATIVE; CYCLOPHELLITOL; NITRILE; NITRILE HYDRATASE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; MUSHROOM; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE;

EID: 78649320288     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.10.010     Document Type: Article

References (31)

1. P. Lalegerie, G. Legler, and J. Yon Biochimie 64 1982 977 999
2. S.G. Withers, and I.P. Street J. Am. Chem. Soc. 110 1988 8551 8553
3. A.D. Elbein Annu. Rev. Biochem. 56 1987 497 534
4. E. Truscheit, W. Frommer, B. Junge, L. Muller, D.D. Schmidt, and W. Wingender Angew. Chem., Int. Ed. Engl. 20 1981 744 761
5. R.A. Gruters, J.J. Neefjes, M. Tersmette, R.E.Y. DeGoede, A. Tulp, H.G. Huisman, F. Miedema, and H.L. Ploegh Nature 350 1987 74 77
6. T. Hudlicky, and M. Cebulak Cyclitols and Their Derivatives 1993 VCH New York
7. S. Atsumi, K. Umezawa, H. Iinuma, H. Naganawa, H. Nakamura, Y. Iitaka, and T. Takeuchi J. Antibiot. 43 1990 49 53
8. S. Atsumi, H. Iinuma, C. Nosaka, and K. Umezawa J. Antibiot. 43 1990 1579 1585
9. S. Atsumi, C. Nosaka, H. Iinuma, and K. Umezawa Arch. Biochem. Biophys. 297 1992 362 367
10. K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, and M. Nakata J. Antibiot. 44 1991 456 458
11. J. Marco-Contelles Eur. J. Org. Chem. 2001 1607 1618
12. K. Tatsuta, Y. Niwata, K. Umezawa, K. Toshima, and M. Nakata Carbohydr. Res. 222 1991 189 203
13. R.E. McDevitt, and B. Fraser-Reid J. Org. Chem. 59 1994 3250 3252
14. K. Sato, M. Bokura, H. Moriyama, and T. Igarashi Chem. Lett. 1994 37 40
15. M.E. Jung, and S.W.T. Choe J. Org. Chem. 60 1995 3280 3281
16. H. Takahashi, T. Iimori, and S. Ikegami Tetrahedron Lett. 39 1998 6939 6942
17. F. Ziegler, and Y. Wang J. Org. Chem. 63 1998 7920 7930
18. A.S. Kireev, A.T. Breithaupt, W. Collins, O.G. Nadein, and A. Kornienki J. Org. Chem. 70 2005 742 745
19. T. Akiyama, H. Shima, M. Ohnari, T. Okazaki, and S. Ozaki Bull. Chem. Soc. Jpn. 66 1993 3760 3767
20. T.K.M. Shing, and V.W.F. Tai J. Chem. Soc., Chem. Commun. 1993 995 996
21. F.G. Hansen, E. Bundgaard, and R. Madsen J. Org. Chem. 70 2005 10139 10142
22. T. Ishikawa, Y. Shimizu, T. Kudoh, and S. Saito Org. Lett. 5 2003 3879 3882
23. R.H. Schlessinger, and C.P. Bergstrom J. Org. Chem. 60 1995 16 17
24. B.M. Trost, D.E. Patterson, and E.J. Hembre Chem. Eur. J. 7 2001 3768 3775
25. N. D'Antona, N. Nicolosi, R. Morrone, D. Kubác, O. Kaplan, and L. Martínková Tetrahedron: Asymmetry 21 2010 695 702
26. Y.U. Kwon, C. Lee, and S.K. Chung J. Org. Chem. 67 2002 3327 3338
27. A.I. Vogel Vogel's Textbook of Practical Organic Chemistry 5th ed. 1989 Longman Harlow pp 671-673
28. C.S. Chen, and C.J. Sih Angew. Chem., Int. Ed. Engl. 28 1989 695 707
29. D. Kubáč, O. Kaplan, V. Elišáková, M. Pátek, V. Vejvoda, K. Slámová, A. Tóthová, M. Lemaire, E. Gallienne, S. Lutz-Wahl, L. Fischer, M. Kuzma, H. Pelantová, S. van Pelt, J. Bolte, V. Křen, and L. Martínková J. Mol. Catal. B: Enzym. 50 2008 107 113
30. M.J. Di Geronimo, and A.D. Antoine Appl. Environ. Microbiol. 31 1976 900 906
31. V. Vejvoda, O. Kaplan, D. Kubáč, V. Křen, and L. Martínková Biocatal. Biotrans. 24 2006 414 418