Probing the Glycosidic Linkage: UV and IR Ion-Dip Spectroscopy of a Lactoside

Journal of the American Chemical Society

Volumn 126, Issue 18, 2004, Pages 5709-5714

  Jockusch, Rebecca A ^a   Kroemer, Romano T ^d   Talbot, Francis O ^a   Snoek, Lavina C ^a   Çarçabal, Pierre ^a   Simons, John P ^a   Havenith, Martina ^c   Bakker, Joost M ^b   Compagnon, Isabelle ^b   Meijer, Gerard ^b,e   Von Helden, Gert ^e  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

^c RUHR UNIVERSITY BOCHUM   (Germany)

^d Pharmacia ^*  (Italy)

^e FRITZ HABER INSTITUT DER MAX PLANCK GESELLSCHAFT   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; GLYCOLS; INFRARED SPECTROSCOPY; SOLUTIONS; SPECTRUM ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

DISACCHARIDES; GAS PHASES; GLYCOCONJUGATES; GLYCOSIDIC LINKAGE;

SUGARS;

BENZYL DERIVATIVE; BENZYL LACTOSIDE; CARBOHYDRATE; DISACCHARIDE; GLYCOCONJUGATE; GLYCOSIDE; LACTOSE; LACTOSIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL BOND; CONFORMATION; GAS; INFRARED SPECTROSCOPY; RIGIDITY; ROTATION; SPECTRUM; ULTRAVIOLET SPECTROSCOPY;

GLYCOSIDES; IONS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 2442427229     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031679k     Document Type: Article

References (35)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
2. Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637-674.
3. Chen, J. Y. J.; Naidoo, K. J. J. Phys. Chem. B 2003, 107, 9558-9566.
4. Naidoo, K. J.; Chen, J. Y. J. Mol. Phys. 2003, 101, 2687-2694.
5. Wormald, M. R.; Petrescu, A. J.; Pao, Y. L.; Glithero, A.; Elliou, T.; Dwek, R. A. Chem. Rev. 2002, 102, 371-386.
6. Imberty, A.; Perez, S. Chem. Rev. 2000, 100, 4567-4588.
7. French, A. D.; Johnson, G. P.; Kelterer, A. M.; Dowd, M. K.; Cramer, C. J. Int. J. Quantum Chem. 2001, 84, 416-425.
8. Strati, G. L.; Willett, J. L.; Momany, F. A. Carbohydr. Res. 2002, 337, 1833-1849.
9. Asensio, J. L.; Jimenez-Barbero, J. Biopolymers 1995, 35, 55-73.
10. Engelsen, S. B.; Koca, J.; Braccini, I.; Dupenhoat, C. H.; Perez, S. Carbohydr. Res. 1995, 276, 1-29.
11. Naidoo, K. J.; Brady, J. W. J. Am. Chem. Soc. 1999, 121, 2244-2252.
12. Jockusch, R. A.; Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1502-1507.
13. Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 3562-3565.
14. Jockusch, R. A.; Kroemer, R. T.; Talbot, F. O.; Simons, J. P. J. Phys. Chem. A 2003, 107, 10725-10732.
15. Hayes, M. L.; Serianni, A. S.; Barker, R. Carbohydr. Res. 1982, 100, 87-101.
16. Cheetham, N. W. H.; Dasgupta, P.; Ball, G. E. Carbohydr. Res. 2003, 338, 955-962.
17. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242.
18. Cloran, F.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 1999, 121, 9843-9851.
19. Engelsen, S. B.; Rasmussen, K. J. Carbohydr. Chem. 1997, 16, 773-788.
20. Espinosa, J. F.; Montero, E.; Vian, A.; Garcia, J. L.; Dietrich, H.; Schmidt, R. R.; Martin-Lomas, M.; Imberty, A.; Canada, F. J.; Jimenez-Barbero, J. J. Am. Chem. Soc. 1998, 120, 1309-1318.
21. Espinosa, J. F.; Canada, F. J.; Asensio, J. L.; Martin-Pastor, M.; Dietrich, H.; Martin-Lomas, M.; Schmidt, R. R.; Jimenez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862-10871.
22. Clark, M.; Cramer, R. D.; van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982-1012.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J. ; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gonzalez, C.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
24. Oepts, D.; van der Meer, A. F. G.; van Amersfoort, P. W. Infrared Phys. Technol. 1995, 36, 297-308.
25. Bakker, J. M.; MacAleese, L.; Meijer, G.; von Helden, G. Phys. Rev. Lett. 2003, 91, art. no. 203003.
26. Bakker, J. M.; MacAleese, L.; von Helden, G.; Meijer, G. J. Chem. Phys. 2003, 119, 11180-11185.
27. Roën, A.; Padrón, J. I.; Vázquez, J. T. J. Org. Chem. 2003, 68, 4615-4630.
28. Rivet, A.; Sabin, C.; Mazeau, K.; Imberty, A.; Perez, S. http://www.cer-mav.cnrs.fr/, accessed May 2003.
29. Stenutz, R.; Shang, M. Y.; Serianni, A. S. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1999, 55, 1719-1721.
30. Juers, D. H.; Heightman, T. D.; Vasella, A.; McCarter, J. D.; Mackenzie, L.; Withers, S. G.; Matthews, B. W. Biochemistry 2001, 40, 14781-14794.
31. Garcia-Herrero, A.; Montero, E.; Munoz, J. L.; Espinosa, J. F.; Vian, A. ; Garcia, J. L.; Asensio, J. L.; Canada, F. J.; Jimenez-Barbero, J. J. Am. Chem. Soc. 2002, 124, 4804-4810.
32. Huisken, F.; Kulcke, A.; Laush, C.; Lisy, J. M. J. Chem. Phys. 1991, 95, 3924-3929.
33. -3) for such monovalent ligands. As such, they are not representative of binding interactions of the entire lactose disaccharide.
34. Although NMR and X-ray crystallography structures of (O-linked) lactose in complex with an inactive mutant of the same enzyme show that the lactose is bound as a trans structure, as detailed in refs 31 and 32.
35. Alzari, P. M.; Souchon, H.; Dominguez, R. Structure 1996, 4, 265-275.