An improved chemical and enzymatic synthesis of new fructose derivatives for import studies by the glucose transporter in parasites

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1557-1572

  Page, Patrick ^a   Blonski, Casimir ^a   Périé, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; FRUCTOSE BISPHOSPHATE ALDOLASE;

ANIMAL TISSUE; ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; MUSCLE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RABBIT; REACTION ANALYSIS; STEREOCHEMISTRY;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0030054153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01001-7     Document Type: Article

References (29)

1. (a) Horecker, B. L.; Tsolas, O.; Lai, C. Y. Enzymes (3rd. Ed.) 1972, 7, 213-258.
2. (b) Meyerhoff, O.; Lohmann, K.; Shuster, P. Biochem. Z. 1936, 286, 319.
3. Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, V. D., Kim, M. J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 627-635.
4. Stereoselective syntheses catalysed by rabbit muscle FDP aldolase have been recently reviewed by Wong et al. . Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412-432.
5. (a) Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 58, 4809-4812.
6. (b) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849-3855.
7. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499-525.
8. Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932.
9. Durrwachter, J. R.; Drueckhammer, D. G.; Nozaki, K.; Sweers, H. M.; Wong, C.-H. J. Am. Chem. Soc. 1986, 108, 7812-7818.
10. Recently 6-deoxy-D-fructose was obtained using Spinach transketolase: Hecquet, L.; Bolte, J.; Demuynck, C. Tetrahedron 1994, 29, 8677-8684.
11. Wong, C.-H.; Mazenod, F. P.; Whitesides, G. M. J. Org. Chem. 1983, 48, 3493-3497.
12. Osten, C. H. von der; Sinskey, A. J.; Barbas, C. F.; Pederson, R. L.; Wang, Y-F.; Wong, C.-H. J. Am. Chem. Soc. 1989, 111, 3924-3927.
13. Durrwachter, J. R.; Wong, C.-H. J. Org. Chem. 1988, 53, 4175-4181.
14. Liu, K. K.-C.; Pederson, R. L.; Wong, C.-H. J. Chem. Soc. Perkin 1 1991, 2669-2673.
15. Eisenthal, R.; Game, S.; Holman, G. D. Biochim. Biophys. Acta 1989, 985, 81-89.
16. Fry, A. F.; Towner, P.; Holman, G. D.; Eisenthal, R. Mol. Biochem. Parasit. 1993, 60, 9-18.
17. Opperdoes, F. R. Annu. Rev. Microbiol. 1987, 41, 127-151.
18. Bischoberger, N.; Waldmann, H.; Saito, T.; Simon, E. S.; Lees, W.; Bednarski, M.; Whitesides, G. M. J. Org. Chem. 1988, 53, 3457-3465.
19. Hanson, R. M.; Chem. Rev. 1991, 91, 437-475.
20. Mitsunobu, O.; Kimura, J.; Ihzumi, K.; Yanagida, N. Bull. Chem. Soc.Japan 1976, 49, 510-513.
21. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602.
22. Pederson, R. L.; Liu, K.K.-C.; Rutan, J. F.; Chen, L.; Wong, C.-H. J. Org. Chem. 1990, 55, 4897-4901
23. Palumbo, G.; Ferreri, C.; Caputo, R. Tetrahedron 1983, 24, 1307-1310.
24. Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Org. Chem. 1987, 52, 667-671.
25. Racha, S.; Li, Z.; El-Subbagh, H.; Abushanab, E. Tetrahedron Lett. 1992, 33, 5491-5494.
26. Li, Z.; Racha, S.; Dan, L.; El-Subbagh, H.; Abushanab, E. J. Org. Chem. 1993, 58, 5779-5583.
27. Que, L.; Gray, G. R. Biochemistry 1974, 13, 146-153.
28. Effenberger, F.; Null, V., Ziegler, T. Tetrahedron Lett. 1992, 33, 5157-5160.
29. Bergmeyer, H. U.; Methods of Enzymatic Analysis, 3rd. Ed. Vol. VI.; Bergmeyer, H. U.; Bermeyer, J.; Grassi, M.;Eds.; Academic Press New York, 1984.