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Nuclear Magnetic Resonance of Glycosides

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Book cover Synthesis and Characterization of Glycosides

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Abstract

Nuclear magnetic resonance (1H, 13C NMR), X-ray diffraction, and mass spectrometry are considered among the most important analytical methods for structural elucidation. Characterization by means of 1H, 13C NMR, mono- and bidimensional spectroscopy is a powerful tool for structural assignment of simple and complex glycosides. Pioneering studies on simple monosaccharides were essential for understanding through the chemical shifts and coupling constants the conformational behavior of sugars.

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References

  1. (a) R.U. Lemieux and A.R. Morgan, Can. J. Chem., 43, 2199 (1965). (b) G. Kotowycz and R.U. Lemieux, Chem. Rev., 73, 669 (1973). (c) R.U. Lemieux and J.D. Stevens, Can. J. Chem., 43, 2059 (1965).

    CAS  Google Scholar 

  2. B. Coxon, Tetrahedron, 21, 3481 (1965).

    Article  CAS  Google Scholar 

  3. (a) L.D. Hall, Adv. Carbohydr. Chem., 19, 51 (1964). (b) L.D. Hall, J.F. Manville, and N.S. Bhacca, Can. J. Chem., 47, 1 (1969).

    CAS  Google Scholar 

  4. D. Horton, and J.H. Lauterbach, Carbohydr. Res., 43, 9 (1975).

    Article  CAS  Google Scholar 

  5. C. Altona, and C.A.G. Haasnoot, Organic Magnetic Resonance, 13, 417 (1980).

    Article  CAS  Google Scholar 

  6. E. Breitmaier, Structure Elucidation by NMR I Organic Chemistry 3th Ed. John Wiley & Sons pp 46 (2002).

    Google Scholar 

  7. M. Karplus, Chem. Phys., 11, 30 (1959).

    Google Scholar 

  8. C.M. Cerda-García-Rojas, L. G. Zepeda, and P. Joseph-Nathan, Tetrahedron Computer Methodology, 3, 113, (1990).

    Article  Google Scholar 

  9. C.V. Holland, D. Horton, M.J. Miller, and N.S. Bhacca, J. Org. Chem., 32, 3077 (1967).

    Article  CAS  Google Scholar 

  10. G. Hajdukovic, M.L. Martin, P. Sinaÿ, and J.R. Pougny, Organic Magnetic Resonance 7, 366 (1975).

    Article  CAS  Google Scholar 

  11. D. Horton and W. N. Turner, J. Org. Chem. 30, 3387 (1965).

    Google Scholar 

  12. K. Bock and H. Thøgerson, Annual Reports on NMR Spectroscopy Ed by G.A Webb, Academic Press 13, 37 (1982).

    Google Scholar 

  13. J. Ø Duus, C.H. Gotffredsen, and K. Bock, Chem. Rev., 100, 4589 (2000).

    Article  CAS  Google Scholar 

  14. A. Delazar, M. Byres, S. Gibbons, Y. Kumarasamy, M. Modarresi, L. Nahar, M. Shoeb, and S. D. Sarker, J. Nat. Prod. 67, 1584 (2004).

    Article  CAS  Google Scholar 

  15. G. Bohr, C. Gerhäuser, J. Knauft, J. Zapp, and H. Becker, J. Nat. Prod. 68, 1545 (2005).

    Article  CAS  Google Scholar 

  16. S.O. Lee, S. Z. Choi, S. U. Choi, K. C. Lee, Y. W. Chin, J. Kim, Y. C. Kim, and K.R. Lee, J. Nat. Prod. 68, 1471 (2005).

    Article  CAS  Google Scholar 

  17. J-H Zou, J.S. Yang, and L. Zhou, J. Nat. Prod. 67, 664 (2004).

    Article  CAS  Google Scholar 

  18. F. Diaz, H-B Chai, Q. Mi, B-N. Su, J.S. Vigo, J.G. Graham, F. Cabieses, N.R. Farnsworth, G.A. Cordell, J.M. Pezzuto, S.M. Swanson, and A. D. Kinghorn, J. Nat. Prod. 67, 352 (2004).

    Article  CAS  Google Scholar 

  19. P. Manitto, D. Monti, and G. Speranza, J. Chem. Soc. Perkin Trans. 1, 1297 (1990).

    Article  Google Scholar 

  20. H. Neubauer, J. Meiler, W. Peti, and C. Griesinger, Helv. Chim. Acta, 84, 243 (2001).

    Article  CAS  Google Scholar 

  21. F. Tian, H.M. Al-Hashimi, J.L. Craighead, and J.H. Prestegard, J. Am. Chem. Soc., 123, 485 (2001).

    Article  CAS  Google Scholar 

  22. A. De Bruyn, J. Carbohydr. Chem., 10, 159 (1991).

    Article  Google Scholar 

  23. R.U. Lemieux and S. Koto, Tetrahedron, 30, 1933 (1974).

    Article  CAS  Google Scholar 

  24. B. Bose, S. Zhao, R. Stenutz, F. Cloran, P.B. Bondo, G. Bondo, B. Hertz, I. Carmichael, and A.S. Serianni, J. Am. Chem. Soc., 120, 11158 (1998).

    Article  CAS  Google Scholar 

  25. K. Bock, A. Brignole., and B.W. Sigurskjold, J. Chem. Soc. Perkin Trans. II, 1711 (1996).

    Google Scholar 

  26. A. Imberty, Current Opinion in Structural Biology, 7, 617 (1997).

    Article  CAS  Google Scholar 

  27. P.K. Agrawal and A.K. Pathak, Phytochemical Analysis, 7, 113 (1996).

    Article  CAS  Google Scholar 

  28. I. Tvaroska, M. Hricovini, and E. Petrakova, Carbohydr. Res., 189, 359 (1989).

    Article  CAS  Google Scholar 

  29. (a) Y.S. Bae, J.F.W. Burger, J.P. Steynberg, D. Ferreira, and R.W. Heminway, Phytochemistry

    Google Scholar 

  30. (a) G. Batta and A. Liptak, J. Am. Chem. Soc., 106, 248 (1984). (b) G. Masiiot, C. Lavaud, C. Delaude, G.V Binst, S.P.F. Miller, and H.M. Fales, Phytochemistry, 29, 3291 (1990).

    Article  CAS  Google Scholar 

  31. J.H. Prestegard, T.A.W. Koerner, P.C. Demou, and R.K. Yu. J. Am. Chem. Soc., 104, 4993 (1982).

    Article  CAS  Google Scholar 

  32. (a) N.M. Duc, R. Kasai, K. Ohtani, A. Ito, N.T. Nham, K. Yamasaki, and O. Tanaka, Chem. Pharm. Bull., 42, 634 (1994). (b) T. Nakamura, T. Takedo, and Y. Ogihara, Chem. Pharm. Bull., 42, 1111 (1994). (c) B. Razanamahefa, C. Demetzos, A.-L Skaltsounis, M. Andriantisiferana, and F. Tillequin, Heterocycles, 38, 357 (1994). (d) T. Nakanishi, K. Tanaka, H. Murata, M. Somekawa, and A. Inada, Chem. Pharm. Bull, 41, 183 (1994). (e) S.T. Thulborg, S.B Christensen, C. Cornett, C.E. Olsen, and E. Lemmich, Phytochemistry, 36, 753 (1994).

    CAS  Google Scholar 

  33. (a) M. Bah and R. Pereda-Miranda, Tetrahedron, 41, 13063 (1996). (b) R. Pereda-Miranda and M. Bah, Current Topics in Medicinal Chemistry, 3, 1 (2003).

    Article  Google Scholar 

  34. B. Coxon, N. Sari, G. Batta, and G. Pozsgay, Carbohydr. Res., 324, 53 (2000).

    Article  CAS  Google Scholar 

  35. H. Sato, and Y. Kajihara, J. Carbohydr. Chem., 22, 339 (2003).

    Article  CAS  Google Scholar 

  36. F.G.J. Vliegenthart, L. Dorland, and H. van Halbeek, Adv. Carbohydr. Chem. Biochem., 41, 209 (1983).

    Article  CAS  Google Scholar 

  37. M. Martin-Lomas and D. Chapman, Chem. Phys, Lipids, 10, 152 (1973).

    Article  CAS  Google Scholar 

  38. (a) J. Dabrowski, P. Handfland, and H. Egge, Biochemistry, 19, 5652 (1980). (b) K.E. Falk, K.-A. Karlsson, and B.E. Samuelson, Arch. Biochem. Biophys., 192, 164 (1979).

    Article  CAS  Google Scholar 

  39. L.S. Wolfe, R.G. Senior, and N.M.K. Ng Yin Kin, J. Biol. Chem., 249, 1838 (1974).

    Google Scholar 

  40. (a) F. Ni, Prog. Nucl. Magn. Reson Spectros., 26, 517 (1994). (b) F. Casset, T. Peters, M. Etzler. E. Korchagina, S. Nifantev, Perez, and A. Imberty, Eur. J. Biochem., 239, 710 (1996).

    Article  CAS  Google Scholar 

  41. (a) T. Peters, and B.M. Pinto, Current Opinion in Structural Biology, 6, 710 (1996). (b) T. Weimar, S.L. Harris,.J.B. Pitnar, K. Bock, and B.M. Pinto, Biochemistry, 34, 13672 (1995).

    Article  CAS  Google Scholar 

  42. K. Scheffler, B. Ernst, A. Katopodis, J.L. Magnani, W.T. Wang, R. Weisemann, and T. Peters, Angew. Chem. Int. Ed., 34, 1841 (1995).

    Article  CAS  Google Scholar 

  43. (a) D.F. Wyss, and J.S. Choi, and G. Wagner, Biochemistry, 34, 1622 (1995). (b) D.F. Wyss, J.S. Choi, J. Li, M.H. Knoppers, K.J. Willis, A.R.N. Arulandaman, A. Smolyar, E.L. Reinherz, and G.Wagner, Science, 269, 1273 (1995). (c) R. Liang, A.H. Androtti, and D. Kahne, J. Am. Chem. Soc., 117, 10395 (1995).

    Article  CAS  Google Scholar 

  44. D. Davies, Progress in NMR Spectroscopy, 12, 140 (1978).

    Google Scholar 

  45. M.H. Sorenssen, C. Nielsen, and P. Nielsen, J. Org. Chem., 66, 4878 (2001).

    Article  CAS  Google Scholar 

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(2007). Nuclear Magnetic Resonance of Glycosides. In: Synthesis and Characterization of Glycosides. Springer, Boston, MA. https://doi.org/10.1007/978-0-387-70792-1_8

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