Comparative 1H NMR and molecular modeling study of hydroxy protons of β-d-Galp-(1→4)-β-d-GlcpNAc-(1→2)-α-d-Manp-(1→O)(CH2)7CH3 analogues in aqueous solution

Carbohydrate Research

Volumn 342, Issue 3-4, 2007, Pages 597-609

  Rohfritsch, Philippe F ^a   Frank, Martin ^a   Sandström, Corine ^b   Kenne, Lennart ^b   Vliegenthart, Johannes F G ^a   Kamerling, Johannis P ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

1H NMR; Hydroxy protons; LacNAc Man; Molecular dynamics simulation; Synthetic analogues

Indexed keywords

AMINES; CHEMICAL MODIFICATION; COMPUTER SIMULATION; HYDROGEN BONDS; HYDROXYLATION; MOLECULAR STRUCTURE;

CHEMICAL SHIFTS; HYDROXY PROTONS; MOLECULAR DYNAMICS SIMULATIONS; SYNTHETIC ANALOGUES;

MOLECULAR DYNAMICS;

ACETIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; GALACTOSE; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

CARBOHYDRATE SEQUENCE; HYDROGEN BONDING; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; TEMPERATURE; TRISACCHARIDES;

EID: 33846511701     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.07.003     Document Type: Article

References (33)

1. Rivera-Sagredo A., Cañada F.J., Nieto O., Jiménez-Barbero J., and Martín-Lomas M. Eur. J. Biochem. 209 (1992) 415-422
2. Solís D., Fernández P., Díaz-Mauriño T., Jiménez-Barbero J., and Martín-Lomas M. Eur. J. Biochem. 214 (1993) 677-683
3. Adams B., and Lerner L.E. J. Am. Chem. Soc. 114 (1992) 4827-4829
4. Leeflang B.R., Vliegenthart J.F.G., Kroon-Batenburg L.M.J., van Eijck B.P., and Kroon J. Carbohydr. Res. 230 (1992) 41-61
5. Poppe L., and van Halbeek H. J. Am. Chem. Soc. 114 (1992) 1092-1094
6. Sheng S., and van Halbeek H. Biochem. Biophys. Res. Commun. 215 (1995) 504-510
7. Brisson J.-R., Uhrinova S., Woods R.J., van der Zwan M., Jarrell H.C., Paoletti L.C., Kasper D.L., and Jennings H.J. Biochemistry 36 (1997) 3278-3292
8. Bekiroglu S., Kenne L., and Sandström C. J. Org. Chem. 68 (2003) 1671-1678
9. Poppe L., and van Halbeek H. J. Am. Chem. Soc. 113 (1991) 363-365
10. Poppe L., Stuike-Prill R., Meyer B., and van Halbeek H. J. Biomol. NMR 2 (1992) 109-136
11. Sandström C., Baumann H., and Kenne L. J. Chem. Soc., Perkin Trans. 2 (1998) 809-815
12. Sandström C., Baumann H., and Kenne L. J. Chem. Soc., Perkin Trans. 2 (1998) 2385-2393
13. Bekiroglu S., Sandström C., Norberg T., and Kenne L. Carbohydr. Res. 328 (2000) 409-418
14. Bekiroglu S., Kenne L., and Sandström C. Carbohydr. Res. 339 (2004) 2465-2468
15. Bekiroglu S., Sandström A., Kenne L., and Sandström C. Org. Biomol. Chem. 2 (2004) 200-205
16. Ivarsson I., Sandström C., Sandström A., and Kenne L. J. Chem. Soc., Perkin Trans. 2 (2000) 2147-2152
17. Felemez M., and Spiess B. J. Am. Chem. Soc. 125 (2003) 7768-7769
18. van Halbeek H., and Poppe L. Magn. Reson. Chem. 30 (1992) S74-S86
19. Kindahl L., Sandström C., Norberg T., and Kenne L. J. Carbohydr. Chem. 19 (2000) 1291-1303
20. Kindahl L., Sandström C., Norberg T., and Kenne L. Carbohydr. Res. 336 (2001) 319-323
21. Harris R., Rutherford T.J., Milton M.J., and Homans S.W. J. Biomol. NMR 9 (1997) 47-54
22. Poppe L., and van Halbeek H. Struct. Biol. 1 (1994) 215-216
23. Rohfritsch P.F., Joosten J.A.F., Krzewinski-Recchi M.-A., Harduin-Lepers A., Laporte B., Juliant S., Cerutti M., Delannoy P., Vliegenthart J.F.G., and Kamerling J.P. Biochim. Biophys. Acta 1760 (2006) 685-692
24. Joosten J.A.F., Evers B., van Summeren R.P., Kamerling J.P., and Vliegenthart J.F.G. Eur. J. Org. Chem. (2003) 3569-3586
25. Haasnoot C.A.G., de Leeuw F.A.A.M., and Altona C. Tetrahedron 36 (1980) 2783-2792
26. Fraser R.R., Kaufman M., Morand P., and Govil G. Can. J. Chem. 47 (1969) 403-409
27. Still W.C., Tempczyk A., Hawley R.C., and Hendrickson T. J. Am. Chem. Soc. 112 (1990) 6127-6129
28. Almond A. Carbohydr. Res. 340 (2005) 907-920
29. Piotto M., Saudek V., and Sklenár V. J. Biomol. NMR 2 (1992) 661-665
30. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., and Still W.C. J. Comput. Chem. 11 (1990) 440-467
31. Case D.A., Cheatham III T.E., Darden T., Gohlke H., Luo R., Merz Jr. K.M., Onufriev A., Simmerling C., Wang B., and Woods R.J. J. Comput. Chem. 26 (2005) 1668-1688
32. Woods R.J., Dwek R.A., Edge C.J., and Fraser-Reid B. J. Phys. Chem. 99 (1995) 3832-3846
33. Frank, M., Conformational Analysis Tools (CAT). http://www.md-simulations.de/CAT/.