Does glycosyl transfer involve an oxacarbenium intermediate? Computational simulation of the lifetime of the methoxymethyl cation in water

Pure and Applied Chemistry

Volumn 83, Issue 8, 2011, Pages 1507-1514

  Williams, Ian H ^a   Pernía, J Javier Ruiz ^a   Tuñón, Iñaki ^b  

^a University of Bath   (United Kingdom)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Computational simulation; Glycosyl transfer; Lifetime; Oxacarbenium ion; Quantum mechanics molecular mechanics (QM MM); Solvent dynamics

Indexed keywords

COMPUTATIONAL SIMULATION; GLYCOSYL; LIFETIME; OXACARBENIUM ION; SOLVENT DYNAMICS;

DYNAMICS; FREE ENERGY; MOLECULAR DYNAMICS; MOLECULAR MODELING; MOLECULES; TWO DIMENSIONAL;

POSITIVE IONS;

EID: 79960854085     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-10-10-12     Document Type: Article

References (33)

1. A. K. J. Chong, M. S. Pegg, N. R. Taylor, M. von Itzstein. Eur. J. Biochem. 207, 335 (1992).
2. N. R. Taylor, M. von Itzstein. J. Med. Chem. 37, 616 (1994).
3. A. G. Watts, I. Damager, M. L. Amaya, A. Buschiazzo, P. Alzari, A. C. Frasch, S. G. Withers. J. Am. Chem. Soc. 125, 7532 (2003).
4. S. L. Newstead, J. A. Potter, J. C. Wilson, G. Xu, C-H. Chien, A. G. Watts, S. G. Withers, G. L. Taylor. J. Biol. Chem. 283, 9080 (2008).
5. D. L. Zechel, S. G. Withers. Acc. Chem. Res. 33, 11 (2000).
6. C. C. F. Blake, L. N. Johnson, G. A. Mair, A. C. T. North, D. C. Phillips, V. R. Sarma. Proc. R. Soc. London B 167, 378 (1967).
7. D. E. Koshland. Biol. Rev. 28, 416 (1953).
8. C. A. Vernon. Proc. R. Soc. London B 167, 389 (1967).
9. A. Fersht. Structure and Mechanism in Protein Science, Freeman (1999).
10. D. J. Vocadlo, G. J. Davies, R. Raine, S. G. Withers. Nature 412, 835 (2001).
11. A. J. Kirby. Nat. Struct. Biol. 8, 737 (2001).
12. T. Islam, M. von Itzstein. Adv. Carbohydr. Chem. Biochem. 61, 293 (2008).
13. M. L. Sinnott. Carbohydrate Chemistry and Biochemistry: Structure and Mechanism, RSC Publishing, Cambridge, UK (2007).
14. T. L. Amyes, W. P. Jencks. J. Am. Chem. Soc. 111, 7888 (1989).
15. A. J. Bennet, T. E. Kitos. J. Chem. Soc., Perkin Trans. 2 1207 (2002)
16. W. P. Jencks. Acc. Chem. Res. 13, 161 (1980).
17. W. P. Jencks. Chem. Soc. Rev. 10, 345 (1981).
18. G. A. Craze, A. J. Kirby, R. Osborne. J. Chem. Soc., Perkin Trans. 2 357 (1978).
19. B. L. Knier, W. P. Jencks. J. Am. Chem. Soc. 102, 6789 (1980).
20. M. J. Field, M. Albe, C. Bret, F. Proust-De Martin, A. Thomas. J. Comput. Chem. 21, 1088 (2000).
21. J. J. Ruiz-Pernía, I. Tuñón, I. H. Williams. J. Phys. Chem. B 114, 5769 (2010).
22. J. J. Ruiz-Pernía, E. Silla, I. Tuñón, S. Martí, V. Moliner. J. Phys. Chem. B 108, 8427 (2004)
23. J. J. Ruiz-Pernía, E. Silla, I. Tuñón, S. Martí. J. Phys. Chem. B 110, 17663 (2006).
24. P. R. Young, W. P. Jencks. J. Am. Chem. Soc. 99, 8238 (1977).
25. D. Laage, J. T. Hynes. J. Phys. Chem. B 112, 14230 (2008).
26. A. Beneduci. J. Mol. Liq. 138, 55 (2008).
27. M. E. S. Soliman, J. J. Ruiz-Pernía, I. R. Greig, I. H. Williams. Org. Biomol. Chem. 7, 5236 (2009).
28. S. Kozmon, I. Tvaroška. J. Am. Chem. Soc. 128, 16921 (2006).
29. A. L. Bowman, I. M. Grant, A. J. Mulholland. Chem. Commun. 4425 (2008).
30. J. Liu, X. Wang, D. Xu. J. Phys. Chem. B 114, 1462 (2010).
31. L. Petersen, A. Ardèvol, C. Rovira, P. J. Reilly. J. Phys. Chem. B 113, 7331 (2009).
32. L. Petersen, A. Ardèvol, C. Rovira, P. J. Reilly. J. Am. Chem. Soc. 132, 8291 (2010).
33. R. Castillo, G. D. Ruggiero, I. H. Williams. Paper in preparation.