Conformational properties of the disaccharide building units of hyaluronan

Carbohydrate Research

Volumn 344, Issue 13, 2009, Pages 1745-1752

  Pogány, Peter ^a   Kovács, Attila ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

Conformation; DFT computations; Hyaluronan; Hydrogen bonding; NBO analysis

Indexed keywords

AQUEOUS SOLUTIONS; BUILDING UNITS; CARBOXYL GROUPS; CARBOXYLATE GROUPS; CONFORMATIONAL PREFERENCES; CONFORMATIONAL PROPERTIES; CONFORMATIONAL SPACE; D-GLUCURONIC ACID; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT COMPUTATIONS; ELECTRON DENSITY DISTRIBUTION; GLUCOSAMINES; HYALURONAN; HYDROGEN BONDING; INTRAMOLECULAR HYDROGEN BONDING; IONIC BONDS; MAIN EFFECT; MULTIPLE BONDING; NBO ANALYSIS; PCM MODEL; SALT FORMATION; SECONDARY INTERACTIONS; SODIUM SALT; STABLE STRUCTURES;

ACIDS; CARBOXYLATION; DENSITY FUNCTIONAL THEORY; GLUCOSE; HYDROGEN; ISOMERS; OXYGEN; POLYSACCHARIDES; PROBABILITY DENSITY FUNCTION; PROTONATION; SALTS;

HYDROGEN BONDS;

CARBOXYL GROUP; CARBOXYLIC ACID; DISACCHARIDE; GLUCOSAMINE DERIVATIVE; GLUCURONIC ACID; HYALURONIC ACID; HYDROGEN; OXYGEN; SODIUM; SODIUM ION;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CONFORMATION; DENSITY; DENSITY FUNCTIONAL THEORY; ELECTRON; HYDROGEN BOND; MODEL; PRIORITY JOURNAL; PROTON TRANSPORT;

ACIDS; CARBOHYDRATE CONFORMATION; DISACCHARIDES; HYALURONIC ACID; MODELS, MOLECULAR; PROTONS; SALTS; SODIUM;

EID: 69149096996     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.05.030     Document Type: Article

References (52)

1. The Biology of Hyaluronan, Ciba Foundation Symposium 143, 1989.
2. Stern R., Asari A.A., and Sugahara K.N. Eur. J. Cell Biol. 85 (2006) 699-715
3. Scott J.E. Biorheology 45 (2008) 209-217
4. Balazs E.A. Curr. Pharm. Biotechnol. 9 (2008) 236-238
5. Hargittai I., and Hargittai M. Struct. Chem. 19 (2008) 697-717
6. Almond A. Cell. Mol. Life Sci. 64 (2007) 1591-1596
7. Cowman M.K., and Matsuoka S. Carbohydr. Res. 340 (2005) 791-809
8. Lapcik Jr. L., Lapcik L., De Smedt S., Demeester J., and Chabrecek P. Chem. Rev. 98 (1998) 2663-2684
9. Laurent T.C., Laurent U.B.G., and Fraser J.R.E. Immunol. Cell. Biol. 74 (1996) A1-A7
10. Atkins E.D.T., Meader D., and Scott J.E. J. Biol. Macromol. 2 (1980) 318-319
11. Holmbeck S.M.A., Petillo P.A., and Lerner L.E. Biochemistry 33 (1994) 14246-14255
12. Scott J.E. FASEB J. 6 (1992) 2639-2645
13. Mitra A.K., Arnott S., and Sheehan J.K. J. Mol. Biol. 169 (1983) 813-827
14. Mitra A.K., Raghunathan S., Sheehan J.K., and Arnott S. J. Mol. Biol. 169 (1983) 829-859
15. Arnott S., Mitra A.K., and Raghunathan S. J. Mol. Biol. 169 (1983) 861-872
16. Sheeehan J.K., Gardner K.H., and Atkins E.D.T. J. Mol. Biol. 117 (1977) 113-135
17. Winter W.T., and Arnott S. J. Mol. Biol. 117 (1977) 761-784
18. Winter W.T., Smith P.J.C., and Arnott S. J. Mol. Biol. 99 (1975) 219-235
19. Guss J.M., Hukins D.W.L., Smith P.J.C., Winter W.T., and Arnott S. J. Mol. Biol. 95 (1975) 359-384
20. Dea I.C.M., Moorhouse R., Rees D.A., Arnott S., Guss J.M., and Balazs E.A. Science 179 (1973) 560-562
21. Atkins E.D.T., and Sheehan J.K. Science 179 (1973) 562-564
22. Atkins E.D.T., and Sheehan J.K. Nat. New Biol. 235 (1972) 253-254
23. Almond A., DeAngelis P.L., and Blundell C.D. J. Mol. Biol. 358 (2006) 1256-1269
24. Blundell C.D., Reed M.A.C., and Almond A. Carbohydr. Res. 341 (2006) 2803-2815
25. Almond A., Colebrooke S.A., DeAngelis P.L., Mahoney D.J., Day A.J., and Blundell C.D. Dynamic Conformational Predictions for Hyaluronan: Using NMR to Confirm Aqueous Simulations. In: Balazs E.A., and Hascall V.C. (Eds). Hyaluronan: Structure, Metabolism, Biological Activities, Therapeutic Applications (2005), Matrix Biology Institute, Edgewater, NJ 3-6
26. Donati A., Magnani A., Bonechi C., Barbucci R., and Rossi C. Biopolymers 59 (2001) 434V445
27. Cavalieri F., Chiessi E., Paci M., Paradossi G., Flaibani A., and Cesaro A. Macromolecules 34 (2001) 99V109
28. Cowman M.K., Feder-Davis J., and Hittner D.M. Macromolecules 34 (2001) 110V115
29. Cowman M.K., Hittner D.M., and Feder-Davis J. Macromolecules 29 (1996) 2894-2902
30. Bayraktar H., Akal E., Sarper O., and Varnali T. J. Mol. Struct. (Theochem) 683 (2004) 121-132
31. Tafi A., Manetti F., Corelli F., Alcaro S., and Botta M. Pure Appl. Chem. 75 (2003) 359-366
32. Almond A., and Sheehan J.K. Glycobiology 13 (2003) 255-264
33. Sheehan, J.; Almond, A. Hyaluronan: Static, Hydrodynamic and Molecular Dynamic Views. In Glyocoforum:Hyaluronan Today; Hascall, V. C., Yanagishita, M., Eds.; Seikagaku Corporation Gycoforum, 2001.
34. Haxaire K., Braccini I., Milas M., Rinuado M., and Pérez S. Glycobiology 10 (2000) 587-594
35. Kaufmann J., Möhle K., Hofmann H.J., and Arnold K. J. Mol. Struct. (Theochem) 422 (1998) 109-121
36. Almond A., Brass A., and Sheehan J.K. Glycobiology 8 (1998) 973-980
37. Almond A., Brass A., and Sheehan J.K. J. Mol. Biol. 284 (1998) 1425-1437
38. Almond A., Sheehan J.K., and Brass A. Glycobiology 7 (1997) 597-604
39. Mo F., and Jensen L.H. Acta Crystallogr., Sect. B 31 (1975) 2867-2873
40. Moulabbi M., Broch H., Robert L., and Vasilescu D. J. Mol. Struct. (Theochem) 395 (1997) 477-508
41. Miertus S., Bella J., Toffanin R., Matulova M., and Paoletti S. J. Mol. Struct. Theochem. 395 (1997) 437-449
42. Nyerges B., and Kovács A. J. Phys. Chem. A 109 (2005) 892-897
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. gaussian 03, Revision D.01, Gaussian: Wallingford, CT, 2004.
44. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
45. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
46. Cossi M., Barone V., Cammi R., and Tomasi J. Chem. Phys. Lett. 255 (1996) 327-335
47. Cammi R., Mennucci B., and Tomasi J. J. Phys. Chem. A 104 (2000) 5631-5637
48. Cossi M., Scalmani G., Rega N., and Barone V. J. Chem. Phys. 117 (2002) 43-54
49. Glendening E.D., Badenhoop J.K., Reed A.E., Carpenter J.E., Bohmann J.A., Morales C.M., and Weinhold F. NBO 5.0 (2001), Theoretical Chemistry Institute, University of Wisconsin, Madison
50. Furlan S., La Penna G., Perico A., and Cesàro A. Carbohydr. Res. 340 (2005) 959-970
51. Almond A., Brass A., and Sheehan J.K. J. Phys. Chem. B 104 (2000) 5634-5640
52. Remko M., and Hricovíni M. Struct. Chem. 18 (2007) 537-547