Hydrogen bonding and cooperativity in isolated and hydrated sugars: Mannose, galactose, glucose, and lactose

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11414-11425

  Çarçabal, Pierre ^a   Jockusc, Rebecca A ^a   Hünig, Isabel ^a   Snoek, Lavina C ^a   Kroemer, Romano T ^b   Davis, Benjamin G ^a   Gamblin, David P ^a   Compagnon, Isabelle ^c   Oomens, Jos ^c   Simons, John P ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b SANOFI   (France)

^c FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CONFORMATIONS; GLUCOSE; HYDRATION; INFRARED RADIATION; PROTEINS; QUANTUM THEORY; RESONANCE; SPECTROSCOPIC ANALYSIS; SUGARS; ULTRAVIOLET RADIATION;

GALACTOSE; INTRAMOLECULAR INTERATION; LACTOSE; MANNOSE;

HYDROGEN BONDS;

CARBOHYDRATE; DISACCHARIDE; GALACTOSE; GLUCOSE; LACTOSE; MANNOSE; MONOSACCHARIDE; WATER;

AB INITIO CALCULATION; ARTICLE; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; QUANTUM CHEMISTRY;

GALACTOSE; GLUCOSE; HYDROGEN BONDING; LACTOSE; MANNOSE; MOLECULAR CONFORMATION; PROTEIN BINDING; WATER;

EID: 23844433966     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0518575     Document Type: Article

References (74)

1. Helenius, A.; Aebi, M. Annu. Rev. Biochem. 2004, 73, 1019-1049.
2. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324.
3. Greenspan, N. S. Curr. Top. Microbiol. Immunol. 2001, 260, 65-85.
4. Jeffrey, G. A. Food Chem. 1996, 56, 241-246.
5. Parra, R. D.; Bulusu, S.; Zeng, X. C. J. Chem. Phys. 2003, 118, 3499-3509.
6. Missopolinou, D.; Panayiotou, C. J. Phys. Chem. A 1998, 102, 3574-3581.
7. Masella, M.; Flament, J. P. Mol. Simul. 2000, 24, 131-156.
8. Gung, B. W.; Zhu, Z. H.; Everingham, B. J. Org. Chem. 1997, 62, 3436-3437.
9. de la Paz, M. L.; Ellis, G.; Perez, M.; Perkins, J.; Jimenez-Barbero, J.; Vicent, C. Eur. J. Org. Chem. 2002, 840-855.
10. de la Paz, M. L.; Gonzalez, C.; Vicent, C. Chem. Commun. 2000, 411-412.
11. de la Paz, M. L.; Jimenez-Barbero, J.; Vicent, C. Chem. Commun. 1998, 465-466.
12. Di Cera, E. Chem. Rev. 1998, 98, 1563-1591.
13. Quiocho, F. A.; Wilson, D. K.; Vyas, N. K. Nature 1989, 340, 404-407.
14. Bhat, T. N.; Bentley, G. A.; Boulot, G.; Greene, M. I.; Tello, D.; Dallacqua, W.; Souchon, H.; Schwarz, F. P.; Mariuzza, R. A.; Poljak, R. J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 1089-1093.
15. Clarke, C.; Woods, R. J.; Gluska, J.; Cooper, A.; Nutley, M. A.; Boons, G. J. J. Am. Chem. Soc. 2001, 123, 12238-12247.
16. Ben-Naim, A. Biophys. Chem. 2002, 101, 309-319.
17. Bottoms, C. A.; Smith, P. E.; Tanner, J. J. Protein Sci. 2002, 11, 2125-2137.
18. Robinson, C. R.; Sugar, S. G. Protein Sci. 1996, 5, 2119-2124.
19. Smithrud, D. B.; Sanford, E. M.; Chao, I.; Ferguson, S. B.; Carcanague, D. R.; Evanseck, J. D.; Houk, K. N.; Diederich, F. Pure Appl. Chem. 1990, 62, 2227-2236.
20. Elgavish, S.; Shaanan, B. J. Mol. Biol. 1998, 277, 917-932 (PDB ID = IAXZ).
21. Ravishankar, R.; Ravindran, M.; Suguna, K.; Surolia, A.; Vijayan, M. Curr. Sci. 1997, 72, 855-861 (PDB ID = 2tep).
22. Ravishankar, R.; Ravindran, M.; Suguna, K.; Surolia, A.; Vijayan, M. Curr. Sci. 1999, 76, 1393-1393 (PDB ID = 2tep).
23. Turton, K.; Natesh, R.; Thiyagarajan, N.; Chaddock, J. A.; Acharya, K. R. Glycobiology 2004, 14, 923-929 (PDB ID = 1UZY).
24. Wormald, M. R.; Petrescu, A. J.; Pao, Y. L.; Glithero, A.; Elliott, T.; Dwek, R. A. Chem. Rev. 2002, 102, 371-386.
25. Heramingsen, L.; Madsen, D. E.; Esbensen, A. L.; Olsen, L.; Engelsen, S. B. Carbohydr. Res. 2004, 339, 937-948.
26. McNamara, J. P.; Muslim, A. M.; Abdel-Aal, H.; Wang, H.; Mohr, M.; Hillier, I. H.; Bryce, R. A. Chem. Phys. Lett. 2004, 394, 429-436.
27. Perez, S.; Imberty, A.; Engelsen, S. B.; Gruza, J.; Mazeau, K.; Jimenez-Barbero, J.; Poveda, A.; Espinosa, J. F.; van Eyck, B. P.; Johnson, G.; French, A. D.; Louise, M.; Kouwijzer, C. E.; Grootenuis, P. D. J.; Bernardi, A.; Raimondi, L.; Senderowitz, H.; Durier, V.; Vergoten, G.; Rasmussen, K. Carbohydr. Res. 1998, 314, 141-155.
28. Perez, S.; Kouwijzer, M.; Mazeau, K.; Engelsen, S. B. J. Mol. Graphics 1996, 14, 307.
29. Woods, R. J. Glycoconjugate J. 1998, 15, 209-216.
30. Arboleda, P. H.; Loppnow, G. R. Anal. Chem. 2000, 72, 2093-2098.
31. Monde, K.; Taniguchi, T.; Miura, N.; Nishimura, S. I. J. Am. Chem. Soc. 2004, 126, 9496-9497.
32. Wen, Z. Q.; Barron, L. D.; Hecht, L. J. Am. Chem. Soc. 1993, 115, 285-292.
33. Hawley, J.; Bampos, N.; Aboitiz, N.; Jimenez-Barbero, J.; de la Paz, M. L.; Sanders, J. K. M.; Carmona, P.; Vicent, C. Eur. J. Org. Chem. 2002, 1925-1936.
34. Bio-active molecules in the gas phase. In Phys. Chem. Chem. Phys.; Simons, J. P., Bowers, M. T., Hobza, P., Weinkauf, R., Ashfold, M. N. R., Eds.; Royal Society of Chemistry: London, 2004; Vol. 6, pp 2543-2890.
35. Jockusch, R. A.; Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1502-1507.
36. Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 3562-3565.
37. Jockusch, R. A.; Kroemer, R. T.; Talbot, F. O.; Snoek, L. C.; Carcabal, P.; Simons, J. P.; Havenith, M.; Bakker, J. M.; Compagnon, I.; Meijer, G.; von Helden, G. J. Am. Chem. Soc. 2004, 126, 5709-5714.
38. Jockusch, R. A.; Kroemer, R. T.; Talbot, F. O.; Simons, J. P. J. Phys. Chem. A 2003, 107, 10725-10732.
39. Robertson, E. G.; Simons, J. P. Phys. Chem. Chem. Phys. 2001, 3, 1-18.
40. Lee, Y. S.; Rho, E. S.; Min, Y. K.; Kim, B. T.; Kim, K. H. J. Carbohydr. Chem. 2001, 20, 503-506.
41. Zemplen, G. Ber. 1920, 60, 1555-1564.
42. Montgomery, E. M.; Richtmyer, N. K.; Hudson, C. S. J. Am. Chem. Soc. 1942, 64, 690-694.
43. Momany, F. A.; Appell, M. D. Abstr. Pap. Am. Chem. Soc. 2003, 226, 080-CARB.
44. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
45. Halgren, T. A. J. Comput. Chem. 1999, 20, 730-748.
46. Frisch, M. J.; et al. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
47. The "clockwise" (c) and "counterclockwise" (cc) directions are defined using the orientation of the standard representation of monosaccharides where the ring oxygen is at the right top corner of the sugar ring as shown all along this report (see Figure 9). For example, the conformation labeled previously "ttt" in βpGlc and βpGal becomes "cc", while "ggg" becomes "c".
48. n is the stretching vibration of OHn.
49. The fact that the pattern cannot be easily seen on the UVUV spectrum of conformer B is due to the weakness of the signal associated with the doublet.
50. -1.
51. acceptor distance and the directionality of the noncovalent interaction, which are provided by the DFT-optimized geometry.
52. Gerhards, M.; Unterberg, C.; Gerlach, A.; Jansen, A. Phys. Chem. Chem. Phys. 2004, 6, 2682-2690.
53. The broad absorption indicated by the red dotted line below the resolved R2PI features shown in Figure 5b probably includes further unresolved vibronic progressions associated with P,U or additional, more weakly populated hydrate structures.
54. Carcabal, P.; Kroemer, R. T.; Snoek, L. C.; Simons, J. P.; Bakker, J. M.; Compagnon, I.; Meijer, G.; von Helden, G. Phys. Chem. Chem. Phys. 2004, 6, 4546-4552.
55. Snoek, L. C.; Kroemer, R. T.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 2130-2139.
56. Momany, F. A.; Appell, M.; Strati, G.; Willett, J. L. Carbohydr. Res. 2004, 339, 553-567.
57. Oepts, D.; van der Meer, A. F. G.; van Amersfoort, P. Infrared Phys. Technol. 1995, 36, 297.
58. -1 below the ccG-g+_ins1 structure. This result supports the view that the phenyl ring does not change, or indeed bias the conformational preferences of hydrated Glc.
59. The conformational landscapes of amino acids can also be severely affected upon complexation with one water molecule as already shown in the case of phenylalanine [Lee, K. T.; Sung, J.; Lee, K. J.; Kim, S. K.; Park, Y. D. J. Chem. Phys. 2002, 116, 8251-8254]
60. and tryptophan [Snoek, L. C.; Kroemer, R. T.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 2130-2139].
61. Bourne, Y.; Astoul, C. H.; Zamboni, V.; Peumans, W. J.; Menu-Bouaouiche, L.; Van Damme, E. J. M.; Barre, A.; Rouge, P. Biochem. J. 2002, 364, 173-180 (PDB ID = 1kuj).
62. Bourne, Y.; Roussel, A.; Frey, M.; Rouge, P.; Fontecillacamps, J. C.; Cambillau, C. Proteins 1990, 8, 365-376 (PDB ID = 11ob).
63. Moothoo, D. N.; Canan, B.; Field, R. A.; Naismith, J. H. Glycobiology 1999, 9, 539-545 (PDB ID = 1bxh).
64. Ng, K. K. S.; Drickamer, K.; Weis, W. I. J. Biol Chem. 1996, 271, 663-674 (PDB ID = 1rdl, 1rdm).
65. Ng, K. K. S.; Kolatkar, A. R.; Park-Snyder, S.; Feinberg, H.; Clark, D. A.; Drickamer, K.; Weis, W. I. J. Biol. Chem. 2002, 277, 16088-16095 (PDB ID = 1kwu).
66. Loris, R.; Van Walle, I.; De Greve, H.; Beeckmans, S.; Deboeck, F.; Wyns, L.; Bouckaert, J. J. Mol. Biol. 2004, 335, 1227-1240 (PDB ID = 1ukg).
67. Sudakevitz, D.; Kostlanova, N.; Blatman-Jan, G.; Mitchell, E. P.; Lerrer, B.; Wimmerova, M.; Katcoff, D. J.; Imberty, A.; Gilboa-Garber, N. Mol. Microbiol. 2004, 52, 691-700 (PDB ID = 1uqx).
68. Naismith, J. H.; Emmerich, C.; Habash, J.; Harrop, S. J.; Helliwell, J. R.; Hunter, W. N.; Raftery, J.; Kalb, A. J.; Yariv, J. Acta Crystallogr., Sect. D 1994, 50, 847-858 (PDB ID = 5cna).
69. Hester, G.; Kaku, H.; Goldstein, I. J.; Wright, C. S. Nat. Struct. Biol. 1995, 2, 472-479 (PDB ID = 1msa).
70. Pratap, J. V.; Jeyaprakash, A. A.; Rani, P. G.; Sekar, K.; Surolia, A.; Vijayan, M. J. Mol. Biol. 2002, 317, 237-247 (PDB ID = Ij4u).
71. de Souza, G. A.; Oliveira, P. S. L.; Trapani, S.; Santos, A. C. O.; Rosa, J. C.; Laure, H. J.; Faca, V. M.; Correia, M. T. S.; Tavares, G. A.; Oliva, G.; Coelho, L.; Greene, L. J. Glycobiology 2003, 13, 961-972 (PDB ID = 1mvq).
72. Hung, C. S.; Bouckaert, J.; Hung, D.; Pinkner, J.; Widberg, C.; DeFusco, A.; Auguste, C. G.; Strouse, R.; Langermann, S.; Waksman, G.; Hultgren, S. J. Mol. Microbiol. 2002, 44, 903-915 (PDB ID = 1kiu).
73. Hester, G.; Wright, C. S. J. Mol. Biol. 1996, 262, 516-531 (PDB ID = 1niv).
74. Harris, S. A.; Gavathiotis, E.; Searle, M. S.; Orozco, M.; Laughton, C. A. J. Am. Chem. Soc. 2001, 123, 12658-12663.