2334
K. Czifra´k et al. / Carbohydrate Research 340 (2005) 2328–2334
}
´
´
´
´
12. Somsak, L.; Kovacs, L.; Toth, M.; Osz, E.; Szilagyi, L.;
1.13. C-(1-Acetamido-1-deoxy-a-D-glucopyranosyl)-
formamide (N-(b-D-gluco-hept-2-ulopyranosylonamide)-
acetamide) (20)
´
´
Gyo¨rgydeak, Z.; Dinya, Z.; Docsa, T.; Toth, B.; Gergely,
P. J. Med. Chem. 2001, 44, 2843–2848.
13. Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395–4421.
14. Schweizer, F. Angew. Chem., Int. Ed. 2002, 41, 230–253.
15. Chrysina, E. D.; Oikonomakos, N. G.; Zographos, S. E.;
Kosmopoulou, M. N.; Bischler, N.; Leonidas, D. D.;
Prepared from 19 (0.1 g, 0.15 mmol) according to Sec-
tion 1.2. Yield: 0.015 g (39%) colourless oil (Rf = 0.29,
1:1 CHCl3–MeOH); [a]D +91 (c 0.396, H2O); 1H
NMR (D2O): d (ppm) 4.12 (1H, ddd, J = 10.1, 4.9,
2.2 Hz, H-5), 3.84 (1H, dd, J = 12.6, 2.2 Hz, H-6), 3.69
(1H, dd, J = 12.6, 4.9 Hz, H-60), 3.68 (1H, d,
J = 9.5 Hz, H-2), 3.63 (1H, dd, J = 9.5, 8.5 Hz, H-3),
3.48 (1H, dd, J = 10.1, 8.5 Hz, H-4), 2.04 (3H, s,
CH3); 13C NMR (D2O): d (ppm) 172.2 (CONH2,
´
´
Kovacs, L.; Docsa, T.; Gergely, P.; Somsak, L. Biocatal.
Biotransform. 2003, 21, 233–242.
16. Krulle, T. M.; Fuente, C.; Watson, K. A.; Gregoriou, M.;
¨
Johnson, L. N.; Tsitsanou, K. E.; Zographos, S. E.;
Oikonomakos, N. G.; Fleet, G. W. J. Synlett 1997, 211–
213.
´
17. Somsak, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11,
1719–1727, Corrigendum 2247.
´
´
´
18. Somsak, L.; Sos, E.; Gyo¨rgydeak, Z.; Praly, J.-P.;
Descotes, G. Tetrahedron 1996, 52, 9121–9136.
19. Grynkiewicz, G.; Bemiller, J. N. Carbohydr. Res. 1983,
112, 324–327.
3JH-2;CONH ¼ 5.7 Hz), 174.7 (NHCO), 85.2 (C-1), 77.1
2
(C-5), 74.1 (C-2), 73.8 (C-3), 69.7 (C-4), 61.5 (C-6),
23.0 (CH3). Anal. Calcd for C37H31N2O11 (680.37):
C, 65.29; H, 4.74; N, 4.12. Found: C, 65.60; H, 4.20;
N, 4.58.
´
´
´
20. Czifrak, K.; Szilagyi, P.; Somsak, L. Tetrahedron: Asym-
metry 2005, 16, 127–141.
21. Suzuki, H.; Takaoka, K. Chem. Lett. 1984, 1733–1736.
´
´
´
22. Gyollai, V.; Somsak, L.; Szilagyi, L. Tetrahedron Lett.
1999, 40, 3969–3972.
23. Hansen, P. E. Prog. Nucl. Magn. Reson. Spectrosc. 1981,
14, 175–296.
Acknowledgements
24. Thomas, W. A. Prog. Nucl. Magn. Reson. Spectrosc. 1997,
30, 183–207.
25. Williamson, R. T.; Marquez, B. L.; Gerwick, W. H.;
This work was supported by the Hungarian Scientific
Research Fund (OTKA T46081). Prof. Dr. P. Gergely
and T. Docsa are thanked for the preliminary kinetic
data, as well as Prof. Dr. N. G. Oikonomakos for help-
ful comments.
´
Ko¨ver, K. E. Magn. Reson. Chem. 2000, 38, 265–273.
´
26. Somsak, L.; Batta, G.; Farkas, I. Carbohydr. Res. 1983,
124, 43–51.
27. Mio, S.; Kumagawa, Y.; Sugai, S. Tetrahedron 1991, 47,
2133–2144.
28. Harrington, P.; Jung, M. E. Tetrahedron Lett. 1994, 35,
5145–5148.
References
29. Sano, H.; Mio, S.; Kitagawa, J.; Shindou, M.; Honma, T.;
Sugai, S. Tetrahedron 1995, 51, 12563–12572.
30. Brandstetter, T. W.; Kim, Y.-h.; Son, J. C.; Taylor, H. M.;
de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.;
Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett.
1995, 36, 2149–2152.
1. Oikonomakos, N. G. Curr. Protein Pept. Sci. 2002, 3, 561–
586.
´
2. Somsak, L.; Nagy, V.; Hadady, Z.; Docsa, T.; Gergely, P.
Curr. Pharma. Design 2003, 9, 1177–1189.
´
3. Somsak, L.; Nagy, V.; Hadady, Z.; Felfo¨ldi, N.; Docsa,
31. Fairbanks, A. J.; Fleet, G. W. J. Tetrahedron 1995, 51,
3881–3894.
T.; Gergely, P. Recent developments in the synthesis and
evaluation of glucose analog inhibitors of glycogen
phosphorylases as potential antidiabetic agents. In Fron-
tiers in Medicinal Chemistry; Reitz, A. B., Kordik, C. P.,
Choudhary, M. I., Rahman, A. u., Eds.; Bentham, 2005;
Vol. 2, pp 253–272.
32. Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Johnson,
L. N.; Crook, S.; Lilley, P. M. Q.; Watkin, D. J.;
Tsitsanou, K. E.; Zographos, S. E.; Chrysina, E. D.;
Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron 1996,
52, 10721–10736.
33. Nakajima, M.; Kirihara, M.; Matsumoto, M.; Katoh, T.;
Terashima, S. Heterocycles 1996, 42, 503–508.
34. Renard, A.; Kotera, M.; Brochier, M.-C.; Lhomme, J.
Eur. J. Org. Chem. 2000, 1831–1840.
35. Shiozaki, M. Carbohydr. Res. 2002, 337, 2077–2088.
36. Estevez, J. C.; Ardron, H.; Wormald, M. R.; Brown, D.;
Fleet, G. W. J. Tetrahedron Lett. 1994, 35, 8889–8890.
37. Estevez, J. C.; Burton, J. W.; Estevez, R. J.; Ardron, H.;
Wormald, M. R.; Dwek, R. A.; Brown, D.; Fleet, G. W. J.
Tetrahedron: Asymmetry 1998, 9, 2137–2154.
38. 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.;
Papageorgioui, A. Biochemistry 1994, 33, 5745–5758.
39. Watson, K. A.; Mitchell, E. P.; Johnson, L. N.; Cruciani,
G.; Son, J. C.; Bichard, C. J. F.; Fleet, G. W. J.;
Oikonomakos, N. G.; Kontou, M.; Zographos, S. E. Acta
Cryst. 1995, D51, 458–472.
4. Wagman, A. S.; Nuss, J. M. Curr. Pharma. Design 2001, 7,
417–450.
5. Moller, D. E. Nature 2001, 414, 821–827.
6. Kurukulasuriya, R.; Link, J. T.; Madar, D. J.; Pei, Z.;
Richards, S. J.; Rohde, J. J.; Souers, A. J.; Szczepan-
kiewicz, B. G. Curr. Med. Chem. 2003, 10, 123–153.
7. Morral, N. Trends Endocrinol. Metab. 2003, 14, 169–
175.
8. Ross, S. A.; Gulve, E. A.; Wang, M. H. Chem. Rev. 2004,
104, 1255–1282.
9. Treadway, J. L.; Mendys, P.; Hoover, D. J. Exp. Opin.
Invest. Drugs 2001, 10, 439–454.
10. 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, 2145–2148.
}
´
´
´
11. Osz, E.; Somsak, L.; Szilagyi, L.; Kovacs, L.; Docsa, T.;
´
Toth, B.; Gergely, P. Bioorg. Med. Chem. Lett. 1999, 9,
1385–1390.