Fructose-1,6-bisphosphate aldolase-mediated synthesis of aminocyclitols (analogues of valiolamine) and their evaluation as glycosidase inhibitors

ChemCatChem

Volumn 1, Issue 4, 2009, Pages 463-471

  El Blidi, Lahssen ^a,b   Assaf, Zeinab ^a,b   Camps Bres, Flora ^a,b   Veschambre, Henri ^a,b   Théry, Vincent ^a,b   Bolte, Jean ^a,b   Lemaire, Marielle ^a,b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b CNRS   (France)

Author keywords

Cyclitols; Enantioselectivity; Enzymes; Glycosylation; Inhibitors

Indexed keywords

ALDOL REACTIONS; AMINOCYCLITOLS; CYCLITOLS; DIHYDROXYACETONE PHOSPHATE; GALACTOSIDASES; GLYCOSIDASE INHIBITORS; INHIBITION PROPERTY; STEREOSELECTIVE METHOD;

CATALYSIS; CONDENSATION REACTIONS; CORROSION INHIBITORS; ENANTIOSELECTIVITY; ENZYMES; GLYCOSYLATION;

FRUCTOSE;

EID: 77951185452     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.200900151     Document Type: Article

References (41)

1. a) Y. Chapleur in Carbohydrate mimics, Wiley-VCH, Weinheim, 1998;
2. X. Chen, Y. Fan, Y. Zheng, Y. Shen, Chem. Rev. 2003, 103, 1955-1977;
3. E. Borges de Melo, A. Da Silveira Gomes, I. Carvalho, Tetrahedron 2006, 62, 10277-10302;
4. A. Delgado, Eur. J. Org. Chem. 2008, 3893-3906.
5. a) N. Sharon, H. Lis, Sci. Am. 1993, 268, 82-90
6. N. Sharon, H. Lis, Science 1989, 246, 227-234
7. A. Kobata, Anal. Biochem. 1979, 100, 1-14;
8. J. Lehmann in Carbohydrates: Structure and Biology, G. Thieme Verlag, Stuttgart, 1998;
9. E. Meléndez-Hevia, T. G. Waddell, E. D. Shelton, Biochem. J. 1993, 295, 477-483;
10. J. J. Marshall, Adv. Carbohydr. Chem. Biochem. 1974, 30, 257-370.
11. a) P. Compain, O. R. Martin, Iminosugars: From Synthesis to Therapeutic Application, Wiley, Chichester, 2007
12. R. J. Nash, in Bioactive Natural Products, 2nd ed. (Eds.: S. M. Colegate, R. J. Molyneux), CRC Press, Boca Raton, FL, 2007, pp. 407-420.
13. Y. Kameda, N. Asano, M. Yoshikawa, K. Matsui, J. Antibiot. 1980, 33, 1575-1576
14. P. Veyssier, A. Bryskier, Antimicrob. Agents Chemother. 2005, 453-469.
15. S. Horii, H. Fuhase, T. Matsuo, Y. Kameda, N. Asano, K. Matsui, J. Med. Chem. 1986, 29, 1038-1046.
16. K. Klumpp, B. J. Graves, Curr. Top. Med. Chem. 2006, 6, 423-434.
17. a) M. Egido-Gabás, D. Canals, J. Casas, A. Llebaria, A. Delgado, Chem- MedChem 2007, 2, 992-994
18. H. Lin, Y. Sugimoto, Y. Ohsaki, H. Ninomiya, A. Oka, M. Taniguchi, H. Ida, Y. Eto, S. Ogawa, Y. Matsuzaki, M. Sawa, T. Inoue, K. Higaki, E. Nanba, K. Ohno, Y. Suzuki, Biochim. Biophys. Acta 2004, 1689, 219-228
19. K. Lei, H. Ninomiya, M. Suzuki, T. Inoue, M. Sawa, M. Iida, H. Ida, Y. Eto, S. Ogawa, K. Ohno, Y. Suzuki, Biochim. Biophys. Acta 2007, 1772, 587-596
20. Y. Suzuki, S. Ichinomiya, M. Kurosawa, M. Ohkubo, H. Watanabe, H. Iwasaki, J. Matsuda, Y. Noguchi, K. Takimoto, M. Itoh, M. Tabe, M. Iida, T. Kubo, S. Ogawa, E. Nanba, K. Higaki, K. Ohno, R. O. Brady, Ann. Neurol. 2007, 62, 671-675
21. Y. Suzuki, Cell. Mol. Life Sci. 2008, 65, 351-353.
22. W.-C. Chou, C. Fotsch, C.-H. Wong, J. Org. Chem. 1995, 60, 2916-2917.
23. a) E. Gallienne, M. Benazza, G. Demailly, J. Bolte, M. Lemaire, Tetrahedron 2005, 61, 4557-4568
24. E. Gallienne, T. Gefflaut, J. Bolte, M. Lemaire, J. Org. Chem. 2006, 71, 894-902.
25. a) L. El Blidi, D. Crestia, E. Gallienne, C. Demuynck, J. Bolte, M. Lemaire, Tetrahedron: Asymmetry 2004, 15, 2951-2954
26. L. El Blidi, M. Ahbala, J. Bolte, M. Lemaire, Tetrahedron: Asymmetry 2006, 17, 2684-2688.
27. For a review see: M. Schümperli, R. Pellaux, S. Panke, Appl. Microbiol. Biotechnol. 2007, 75, 33-45 and references therein.
28. a) A. Siebum, A. Van Wijk, R. Schoevaart, T. Kieboom, J. Mol. Catal. B 2006, 41, 141-145
29. D. Franke, T. Machajewski, C.-C. Hsu, C.-H. Wong, J. Org. Chem. 2003, 68, 6828-6831.
30. M. Sugiyama, Z. Hong, P.-H. Liang, S. M. Dean, L. J. Whalen, W. A. Greenberg, C.-H. Wong, J. Am. Chem. Soc. 2007, 129, 14811-14817
31. A. L. Concia, C. Lozano, J. A. Castillo, T. Parella, J. Joglar, P. Clapés, Chem. Eur. J. 2009, 15, 3808-3816.
32. a) R. Ballini, L. Barboni, F. Fringuelli, A. Palmieri, F. Pizzo, L. Vaccaro, Green Chem. 2007, 9, 823-838
33. F. A. Luzzio, Tetrahedron 2001, 57, 915-945.
34. F. Charmantray, L. El Blidi, T. Gefflaut, L. Hecquet, J. Bolte, M. Lemaire, J. Org. Chem. 2004, 69, 9310-9312.
35. R. Chênevert, S. Gravil, J. Bolte, Tetrahedron: Asymmetry 2005, 16, 2081-2086.
36. Sybyl package, Tripos Inc., St. Louis, MO.
37. Gaussian 03, Revision D.03, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian Inc., Wallingford, CT, 2004.
38. a) P. Hohenberg, W. Kohn, Phys. Rev. B 1964, 136, 864
39. W. Kohn, L. J. Sham, Phys. Rev. A 1965, 140, 1133.
40. a) R. Cammi, B. Mennucci, J. Tomasi, J. Phys. Chem. A 2000, 104, 5631-5637
41. M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comput. Chem. 2003, 24, 669-681.