7-Carbon mimics of D-glucose and L-fucose: Activation of 6R-, and inactivation of 6S-, -6C-methylglucose of glycogen synthase: Inhibition of glucokinase and/or glucose-6-phosphatase

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7155-7158

  Blériot, Yves ^a   Smelt, Kathryn H ^a   Cadefau, Joan ^b   Bollen, Mathieu ^b   Stalmans, Willy ^b   Biggadike, Keith ^c   Johnson, Louise N ^d   Oikonomakos, Nikos G ^e   Lane, Alexandra L ^d   Crook, Sarah ^d   Watkin, David J ^d   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c GLAXOSMITHKLINE   (United Kingdom)

^d UNIVERSITY OF OXFORD   (United Kingdom)

^e INSTITUTE OF BIOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLUCOKINASE; GLUCOSE 6 PHOSPHATASE; GLYCOGEN SYNTHASE; GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342683712     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01565-1     Document Type: Article

References (25)

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8. 6. Watson, K. A., Mitchell, E. P., Johnson, L. N., Son, J. C., Bichard, C. J. F., Orchard, M. G., Fleet, G. W. J., Oikonomakos, N. G., Leonidas, D. D., Kontou, M., Papageoriouo, A., Biochemistry, 1994, 33, 5745; Watson, K. A., Mitchell, E. P., Johnson, L. N., Son, J. C., Bichard, C. J. F., Fleet, G. W. J., Oikonomakos, N. G., Kontou, M., Zographos, S. E., Acta Cryst. Sect. D, 1995, 51, 458; Board, M., Bollen, M., Stalmans, W., Kim, Y., Fleet, G. W. J., Johnson, L. N., Biochem. J., 1995, 311, 845; Bichard, C. J. F., Mitchell, E. P., Wormald, M. R., Watson, K. A., Johnson, L. N., Zographos, S. E., Koutra, D. D., Oikonomakos, N. G., Fleet, G. W. J., Tetrahedron Lett., 1995, 36, 2145.
9. 6. Watson, K. A., Mitchell, E. P., Johnson, L. N., Son, J. C., Bichard, C. J. F., Orchard, M. G., Fleet, G. W. J., Oikonomakos, N. G., Leonidas, D. D., Kontou, M., Papageoriouo, A., Biochemistry, 1994, 33, 5745; Watson, K. A., Mitchell, E. P., Johnson, L. N., Son, J. C., Bichard, C. J. F., Fleet, G. W. J., Oikonomakos, N. G., Kontou, M., Zographos, S. E., Acta Cryst. Sect. D, 1995, 51, 458; Board, M., Bollen, M., Stalmans, W., Kim, Y., Fleet, G. W. J., Johnson, L. N., Biochem. J., 1995, 311, 845; Bichard, C. J. F., Mitchell, E. P., Wormald, M. R., Watson, K. A., Johnson, L. N., Zographos, S. E., Koutra, D. D., Oikonomakos, N. G., Fleet, G. W. J., Tetrahedron Lett., 1995, 36, 2145.
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16. 2O + dioxan): 19.3 (q, Me), 19.5 (q, Me), 65.0, 65.1, 70.4, 70.6, 72.3, 73.8, 74.0, 75.1, 76.8, 78.5 (10 x d, C-2, C-3, C-4, C-5, C-6 α and β), 92.8 (d, C-1α), 96.9 (d, C-1β).
17. 11. The details of the crystal structures of 11 and 13 will be presented in the full paper.
18. 2O + dioxan): 14.7 (q, Me), 14.8 (q, Me), 66.1, 70.5, 70.7, 71.2, 72.8, 72.9, 74.0, 75.7, 77.7 (9 x d, C-2, C-3, C-4, C-5, C-6 α and β), 91.9 (d, C-1α), 96.0 (d, C-1β).
19. 13. Ichikawa, Y., Halcomb, R. L., Wong, C.-H., Chem. in Brit., 1994, 117.
20. 14. Assay of glycogen phosphorylase: Watson, K. A., Mitchell, E. P., Johnson, L. N., Son, J. C., Bichard, C. J. F., Fleet, G. W. J., Oikonomakos, N. G., Kontou, M., Zographos, S. E., Acta Cryst. Sect. D, 1995, 51, 458 and references cited therein.
21. 15. Assay for glycogen synthase: Dopere, F., Vanstapel, F., Stalmans, W., Eur. J. Biochem., 1980, 104, 137. Assay for Glc-6-P: Lowry, O. H., Passonneau, J. V., A flexible system of enzymatic analysis, Academic Press, New York, pp. 71-77, 1972. Assay for glucokinase: Davidson A. L., Arion, W. J., Arch. Biochem. Biophys., 1987, 253, 156. Assay for Glc-6-Pase: Burchell, A., Hume, R., Burchell, B., Clin. Chim. Acta, 1988, 173, 183.
22. 15. Assay for glycogen synthase: Dopere, F., Vanstapel, F., Stalmans, W., Eur. J. Biochem., 1980, 104, 137. Assay for Glc-6-P: Lowry, O. H., Passonneau, J. V., A flexible system of enzymatic analysis, Academic Press, New York, pp. 71-77, 1972. Assay for glucokinase: Davidson A. L., Arion, W. J., Arch. Biochem. Biophys., 1987, 253, 156. Assay for Glc-6-Pase: Burchell, A., Hume, R., Burchell, B., Clin. Chim. Acta, 1988, 173, 183.
23. 15. Assay for glycogen synthase: Dopere, F., Vanstapel, F., Stalmans, W., Eur. J. Biochem., 1980, 104, 137. Assay for Glc-6-P: Lowry, O. H., Passonneau, J. V., A flexible system of enzymatic analysis, Academic Press, New York, pp. 71-77, 1972. Assay for glucokinase: Davidson A. L., Arion, W. J., Arch. Biochem. Biophys., 1987, 253, 156. Assay for Glc-6-Pase: Burchell, A., Hume, R., Burchell, B., Clin. Chim. Acta, 1988, 173, 183.
24. 15. Assay for glycogen synthase: Dopere, F., Vanstapel, F., Stalmans, W., Eur. J. Biochem., 1980, 104, 137. Assay for Glc-6-P: Lowry, O. H., Passonneau, J. V., A flexible system of enzymatic analysis, Academic Press, New York, pp. 71-77, 1972. Assay for glucokinase: Davidson A. L., Arion, W. J., Arch. Biochem. Biophys., 1987, 253, 156. Assay for Glc-6-Pase: Burchell, A., Hume, R., Burchell, B., Clin. Chim. Acta, 1988, 173, 183.
25. 16. Support has been received for a Graduate Studentship from GlaxoWellcome and Post-doctoral fellowships from EPSRC and European Community contract BIO2 CT94 3025