Disordered hydrogen bonding in N-(1-deoxy-β-d-fructopyranos-1-yl)-N-allylaniline

Carbohydrate Research

Volumn 344, Issue 7, 2009, Pages 948-951

  Mossine, Valeri V ^a   Barnes, Charles L ^b   Mawhinney, Thomas P ^a  

^a University of Missouri   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

Amadori compound; Crystal structure; d Fructose N allylaniline; Flip flop hydrogen bonding

Indexed keywords

AMADORI COMPOUND; AVERAGE VALUES; CHAIR CONFORMATIONS; CRYSTALLINE STATE; D-FRUCTOSE-N-ALLYLANILINE; FLIP-FLOP HYDROGEN BONDING; FRUCTOPYRANOSE; FURANOSE; HYDROGEN ATOMS; HYDROXYL GROUPS; INTERMOLECULAR HYDROGEN BONDINGS; PYRANOSE; SINGLE-CRYSTAL X-RAY DIFFRACTIONS; VALENCE ANGLES;

CARBOHYDRATES; CONFORMATIONS; CRYSTAL STRUCTURE; CRYSTALLINE MATERIALS; FLIP FLOP CIRCUITS; FRUCTOSE; HYDROGEN; OZONE WATER TREATMENT;

HYDROGEN BONDS;

ALPHA FURANOSE; ALPHA PYRANOSE; ANILINE DERIVATIVE; BETA FURANOSE; BETA PYRANOSE; CARBOHYDRATE DERIVATIVE; N (1 DEOXY BETA DEXTRO FRUCTOPYRANOS 1 YL) N ALLYLANILINE; UNCLASSIFIED DRUG;

AMADORI REARRANGEMENT; ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; X RAY DIFFRACTION;

FRUCTOSE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; X-RAY DIFFRACTION;

EID: 64949108060     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.02.017     Document Type: Article

References (32)

1. Paulsen H., and Pflughaupt K.-W. In: Pigman W., and Horton D. (Eds). The Carbohydrates Chemistry and Biochemistry Vol. IB (1980), Academic Press, NY 881-927
2. Mills F.D., Baker B.G., and Hodge J.E. J. Agric. Food Chem. 17 (1969) 723-727
3. Feather M.S. Comments Agric. Food Chem. 3 (1994) 69-85
4. Bry L., Chen P.C., and Sacks D.B. Clin. Chem. 47 (2001) 153-163
5. Monnier V.M., Sell D.R., Dai Z., Nemet I., Collard F., and Zhang J. Ann. N.Y. Acad. Sci. 1126 (2008) 81-88
6. Mossine V.V., Glinsky V.V., and Mawhinney T.P. In: Klyosov A.A., Witczak Z.J., and Platt D. (Eds). Galectins (2008), John Wiley & Sons, Hoboken, N. J. 235-270
7. Mossine V.V., Chopra P., and Mawhinney T.P. Cancer Res. 68 (2008) 4384-4391
8. Altena J.H., van den Ouweland G.A.M., Teunis C.J., and Tjan S.B. Carbohydr. Res. 92 (1981) 37-49
9. Röper H., Röper S., Heyns K., and Meyer B. Carbohydr. Res. 116 (1983) 183-195
10. Mossine V.V., Linetsky M., Glinsky G.V., Ortwerth B.J., and Feather M.S. Chem. Res. Toxicol. 12 (1999) 230-236
11. Angyal S.J., Bethell G.S., Cowley D.E., and Pickles V.A. Aust. J. Chem. 29 (1976) 1239-1247
12. Jones N.A., Jenkinson S.F., Soengas R., Fanefjord M., Wormald M.R., Dwek R.A., Kiran G.P., Devendar R., Takata G., Morimoto K., Izumori K., and Fleet G.W.J. Tetrahedron: Asymmetry 18 (2007) 774-786
13. Szarek W.A., Rafka R.J., Yang T.-F., and Martin O.R. Can. J. Chem. 73 (1995) 1639-1644
14. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1357
15. French A.D., Dowd M.K., and Reilly P.J. J. Mol. Struct. 395-396 (1997) 271-287
16. Mossine V.V., Glinsky G.V., and Feather M.S. Carbohydr. Res. 262 (1994) 257-270
17. Craig D.C., Stephenson N.C., and Stevens J.D. Cryst. Struct. Commun. 3 (1974) 277-281
18. Kanters J.A., Roelofsen G., Alblas B.P., and Meinders I. Acta Crystallogr., Sect. B 33 (1977) 665-672
19. Mossine V.V., Glinsky G.V., Barnes C.L., and Feather M.S. Carbohydr. Res. 266 (1995) 5-14
20. Tarnawski M., Slepokura K., Lis T., Kulis-Orzechowska R., and Szelepin B. Carbohydr. Res. 342 (2007) 1264-1270
21. Mossine V.V., Barnes C.L., and Mawhinney T.P. Carbohydr. Res. 342 (2007) 131-138
22. Mossine V.V., Barnes C.L., and Mawhinney T.P. J. Carbohydr. Chem. 26 (2007) 249-266
23. Rodriguez R., Cobo J., Nogueras M., Low J.N., and Glidewell C. Acta Crystallogr., Sect. C 63 (2007) o507-o509
24. Jeffrey G.A., and Taylor R. J. Comput. Chem. 1 (1980) 99-109
25. Harding C.C., Cowley A.R., Watkin D.J., Punzo F., Hotchkiss D., and Fleet G.W.J. Acta Crystallogr., Sect. E 61 (2005) o1475-o1477
26. Steiner T., Mason S.A., and Saenger W. J. Am. Chem. Soc. 113 (1991) 5676-5687
27. Saenger W., Betzel C., Hingerty B., and Brown G.M. Nature 296 (1982) 581-583
28. Caruso F., Tanski J., Villegas-Estrada A., and Rossi M. J. Agric. Food Chem. 52 (2004) 7279-7285
29. Dieleman C.B., Marsol C., Matt D., Kyritsakas N., Harriman A., and Kintzinger J.-P. J. Chem. Soc., Dalton Trans. (1999) 4139-4148
30. Sheldrick G.M. shelxs-97, Crystal Structure Solution (1997), University of Göttingen
31. Sheldrick G.M. shelxl-97, Crystal Structure Refinement (1997), University of Göttingen
32. Barbour L. J. Supramol. Chem. 1 (2001) 189-191