Isotope effect-mapping of the ionization of glucose demonstrates unusual charge sharing

Journal of the American Chemical Society

Volumn 125, Issue 26, 2003, Pages 7872-7877

  Lewis, Brett E ^a   Schramm, Vern L ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPE EFFECT;

IONIZATION; ISOTOPES; PH EFFECTS; RATE CONSTANTS; TITRATION;

GLUCOSE;

ANION; ANION EXCHANGE RESIN; CARBON 14; GLUCOSE; HYDROGEN; ISOTOPE; PYRANOSE; TRITIUM; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANION EXCHANGE CHROMATOGRAPHY; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRIC POTENTIAL; EQUILIBRIUM CONSTANT; FRACTIONATION; GAS; IONIZATION; ISOTOPE LABELING; PH; PKA; SUBSTITUTION REACTION; TITRIMETRY; TRANSPORT KINETICS;

ANIONS; CARBON ISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; GLUCOSE; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRANS; SOLUTIONS; TRITIUM; WATER;

EID: 0037526888     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034983m     Document Type: Article

References (27)

1. Lockley, W. J. S. J. Chromatogr. 1989, 483, 413.
2. Tanaka, N.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 1617.
3. Baweja, R. J. Liq. Chromatogr. 1986, 9, 2609.
4. Lowry, T. M.; Faulkner, I. J. J. Chem. Soc. 1925, 127, 2539.
5. Lowry, T. M.; Smith, G. F. J. Chem. Soc. 1927, 2539.
6. Lowry, T. M. J. Chem. Soc. 1927, 2554.
7. Bronsted, J. N.; Guggenheim, E. A. J. Am. Chem. Soc. 1927, 49, 2554.
8. Hudson, C. S. J. Am. Chem. Soc. 1910, 32, 889.
9. Urban, F.; Shaffer, P. A. J. Biol. Chem. 1931, 94, 697.
10. El Khadem, H. S.; Ennifar, S.; Isbell, H. S. Carbohydr. Res. 1989, 185, 51.
11. Rendleman, J. A. J. Adv. Carbohydr. Chem. 1966, 21, 209.
12. Rendleman, J. A. J. J. Org. Chem. 1966, 31, 1839.
13. Rendleman, J. A. J. J. Org. Chem. 1966, 31, 1846.
14. Cochran, W. Nature 1946, 157, 872.
15. Beevers, C. A.; Cochran, W. Proc. R. Soc. London, Ser. A 1947, 190, 257.
16. Söderman, P.; Widmalm, G. J. Org. Chem. 1999, 64, 4199.
17. Lewis, B. E.; Schramm, V. L. J. Am. Chem. Soc. 2003, 125, 4785.
18. 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; 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.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
19. Paneth, P. "ISOEFF98", 1998.
20. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
21. Lewis, B. E.; Schramm, V. L. J. Am. Chem. Soc. 2001, 123, 1327.
22. Zhu, Z.; Zajicek, J.; Serianni, A. S. J. Org. Chem. 2001, 66, 6244.
23. Rohrer, J. S.; Olechno, J. D. Anal. Chem. 1992, 64, 914.
24. Kudelin, B. K.; Gavrilina, L. V.; Kaminski, Y. L. J. Chromatogr. 1993, 636, 243.
25. de Ridder, J. J.; van Hal, H. J. M. J. Chromatogr. 1976, 121, 96.
26. Masters, C. F.; Markey, S. P.; Mefford, I. N.; Duncan, M. W. Anal. Chem. 1988, 60, 2131.
27. Heys, J. R. J. Chromatogr. 1987, 407, 37.