The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2761-2772

  Blériot, Yves ^a   Veighey, Clifford R ^a   Smelt, Kathryn H ^a   Cadefau, Joan ^b   Stalmans, Willy ^b   Biggadike, Keith ^c   Lane, Alexandra L ^d   Müller, Matthias ^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)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOKINASE; GLUCOSE DERIVATIVE; SUGAR;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOISOMERISM; X RAY ANALYSIS;

EID: 0030249951     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00356-4     Document Type: Article

References (31)

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14. 10 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; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10711; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Chrysina, E. D., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10720.
15. 10 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; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10711; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Chrysina, E. D., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10720.
16. 10 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; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10711; Brandstetter, T. W., de la Fuente, C., Kim, Y.-H., Crook, S., Lilley, P. M. de Q., Watkin, D. J., Tsitsanou, K. E., Zographos, S. E., Chrysina, E. D., Oikonomakos, N. G., Johnson, L. N., Fleet, G. W. J., Tetrahedron, 1996, 52, 10720.
17. 11 Kitihara, T., Ogawa, T., Naganuma, T., Matsui, M., Agr. Biol. Chem., 1974, 38, 2189; Bashyal, B. P., Chow, H.-F., Fleet, G. W. J., Tetrahedron, 1987, 43, 423.
18. 11 Kitihara, T., Ogawa, T., Naganuma, T., Matsui, M., Agr. Biol. Chem., 1974, 38, 2189; Bashyal, B. P., Chow, H.-F., Fleet, G. W. J., Tetrahedron, 1987, 43, 423.
19. 12 Pigman, W., Horton, D., Carbohydrates - Their Chemistry and Biochemistry, p. 166, Academic Press, New York, 1972.
20. 13 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. Assay for glycogen phosphorylase: Vandebroeck, A., Bollen, M., De Wulf, H., Stalmans, W., Eur. J. Biochem., 1985, 153, 621.
21. 13 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. Assay for glycogen phosphorylase: Vandebroeck, A., Bollen, M., De Wulf, H., Stalmans, W., Eur. J. Biochem., 1985, 153, 621.
22. 13 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. Assay for glycogen phosphorylase: Vandebroeck, A., Bollen, M., De Wulf, H., Stalmans, W., Eur. J. Biochem., 1985, 153, 621.
23. 13 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. Assay for glycogen phosphorylase: Vandebroeck, A., Bollen, M., De Wulf, H., Stalmans, W., Eur. J. Biochem., 1985, 153, 621.
24. 13 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. Assay for glycogen phosphorylase: Vandebroeck, A., Bollen, M., De Wulf, H., Stalmans, W., Eur. J. Biochem., 1985, 153, 621.
25. 14 Support has been received for a Graduate Studentship from GlaxoWellcome and Post-doctoral fellowships from EPSRC and European Community contract BIO2 CT94 3025.
26. 15 Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., in preparation.
27. 16 Watkin, D.J. Prout, C.K., Carruthers, J.R., Betteridge, P.W., CRYSTALS Issue 10, Chemical Crystallography Laboratory, University of Oxford, Oxford, 1996.
28. 17 Watkin, D.J. Prout, C.K., Pearce, L.J., CAMERON, Chemical Crystallography Laboratory, University of Oxford, Oxford.
29. 18 International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, 1992.
30. 19 The atomic coordinates for 1β and 10 are available on request from the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW; the crystallographic numbering system differs from that used elsewhere in the text. Any request should be accompanied by the full literature citation for this paper.
31. 20 Prince, E., Mathematical Techniques in Crystallography and Material Sciences, Springer-Verlag Inc., New York, 1992.