Enzymatic synthesis of 3-deoxy-D-manno-2-octulosonic acid and analogues: A new approach by a non metabolic pathway

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4181-4182

  Guérard, Christine ^a   Demuynck, Colette ^a   Bolte, Jean ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXYMANNO 2 OCTULOSONIC ACID; 4 DEOXYMANNO OCTULOSONIC ACID; ALDEHYDE; DIHYDROXYACETONE PHOSPHATE; FRUCTOSE BISPHOSPHATE ALDOLASE; GLYCERALDEHYDE 3 PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENZYME SYNTHESIS; STEREOCHEMISTRY;

EID: 0033612172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00709-1     Document Type: Article

References (17)

1. Unger, F. M. Adv. Carbohydr. Chem. Biochem. 1981, 38, 323-388.
2. Danishefsky, S. J.; De Ninno, M. P.; Chen, S.; J. Am. Chem. Soc. 1988, 110, 3929-3940.; Lubineau, A.; Augé, J.; Lubin, N. Tetrahedron, 1993, 49, 4639-4650.
3. Danishefsky, S. J.; De Ninno, M. P.; Chen, S.; J. Am. Chem. Soc. 1988, 110, 3929-3940.; Lubineau, A.; Augé, J.; Lubin, N. Tetrahedron, 1993, 49, 4639-4650.
4. Ghalambor, M. A.; Levine, E. M.; Heath, E. C. J. Biol. Chem., 1966, 241, 3207-3215.; Frick, W.; Krülle, T.; Schmidt, R. R. Liebigs Ann. Chem., 1991, 435-438.
5. Ghalambor, M. A.; Levine, E. M.; Heath, E. C. J. Biol. Chem., 1966, 241, 3207-3215.; Frick, W.; Krülle, T.; Schmidt, R. R. Liebigs Ann. Chem., 1991, 435-438.
6. Hammond, S. M.; Claesson, A.; Jansson, A. M.; Larsson, L. G.; Pring, B. G.; Town, C. M.; Ekström, B. Nature, 1987, 327, 730-732.; Goldman, R.; Kohlbrenner, W.; Lartey, P. A.; Pernet, P Nature, 1987, 329, 162-164.
7. Hammond, S. M.; Claesson, A.; Jansson, A. M.; Larsson, L. G.; Pring, B. G.; Town, C. M.; Ekström, B. Nature, 1987,327, 730-732.; Goldman, R.; Kohlbrenner, W.; Lartey, P. A.; Pernet, P Nature, 1987, 329, 162-164.
8. Bednarski, M. D.; Crans, D. C.; Di Cosimo, R.; Simon, E. S.; Stein, P. D.; Whitesides, G. M. Tetrahedron Lett., 1988, 29, 427-430.
9. Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc., 1993, 115, 413-421.; Kragl, U.; Gödde, A.; Wandrey, C.; Lubin, N.; Augé, C. J. Chem. Soc. Perkin Trans. I, 1994, 119-124.
10. Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc., 1993, 115, 413-421.; Kragl, U.; Gödde, A.; Wandrey, C.; Lubin, N.; Augé, C. J. Chem. Soc. Perkin Trans. I, 1994, 119-124.
11. Augé, C.; Delest, V. Tetrahedron Asym., 1995, 6, 863-866.
12. André, C.; Demuynck, C.; Gefflaut, T.; Guérard, C.; Hecquet, L.; Lemaire, L.; Bolte, J. J. Mol. Catal. B. 1998, 5, 113-118
13. Wong, C.-H.; Whitesides, G.M.; 1994, in "Enzymes in Synthetic Organic Chemistry", Bergamon: Oxford, 195.
14. Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron Asym., 1997, 8, 3895-3902.
15. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc., 1994, 116, 1821-1830.
16. DHAP was prepared and assayed according to Gefflaut, T.; Lemaire, M.; Valentin, M.-L.; Bolte, J. J. Org. Chem. 1997, 62, 5920-5922.
17. 2 olefin); 142.4 (C2); 172.3 (C1); 215.8 (C7).