The molecular mechanism of enzymatic glycosyl transfer with retention of configuration: Evidence for a short-lived oxocarbenium-like species

Angewandte Chemie - International Edition

Volumn 50, Issue 46, 2011, Pages 10897-10901

  Ardèvol, Albert ^a   Rovira, Carme ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

computational chemistry; glycosides; reaction mechanisms; transferases; transition states

Indexed keywords

ANOMERIC CONFIGURATION; GLYCOSYL; METADYNAMICS; MOLECULAR MECHANISM; QUANTUM LEAPS; REACTION MECHANISMS; TRANSFERASES; TRANSITION STATE;

MOLECULAR MODELING; SUGARS;

COMPUTATIONAL CHEMISTRY;

CARBENE; DRUG DERIVATIVE; ENZYME; GLUCOSYLTRANSFERASE; GLYCOSYLTRANSFERASE; ION; METHANE; TREHALOSE 6 PHOSPHATE SYNTHETASE; TREHALOSE-6-PHOSPHATE SYNTHASE;

ARTICLE; CHEMISTRY; METABOLISM; MOLECULAR DYNAMICS; QUANTUM THEORY;

ENZYMES; GLUCOSYLTRANSFERASES; GLYCOSYLTRANSFERASES; IONS; METHANE; MOLECULAR DYNAMICS SIMULATION; QUANTUM THEORY;

EID: 80855133537     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104623     Document Type: Article

References (30)

1. D. J. Vocadlo, G. J. Davies, Curr. Opin. Chem. Biol. 2008, 12, 539-555.
2. L. L. Lairson, B. Henrissat, G. J. Davies, S. G. Withers, Annu. Rev. Biochem. 2008, 77, 521-555.
3. L. N. Gastinel, C. Bignon, A. K. Misra, O. Hindsgaul, J. H. Shaper, D. H. Joziasse, EMBO J. 2001, 20, 638-649.
4. A. Monegal, A. Planas, J. Am. Chem. Soc. 2006, 128, 16030-16031.
5. N. Soya, Y. Fang, M. M. Palcic, J. S. Klassen, Glycobiology 2011, 21, 547-552.
6. I. Andre, I. Tvaroska, J. P. Carver, Carbohydr. Res. 2003, 338, 865-877.
7. M. L. Sinnott, Chem. Rev. 1990, 90, 1171-1202.
8. K. Persson, H. D. Ly, M. Dieckelmann, W. W. Wakarchuk, S. G. Withers, N. C. Strynadka, Nat. Struct. Biol. 2001, 8, 166-175.
9. M. L. Sinnott, W. P. Jencks, J. Am. Chem. Soc. 1980, 102, 2026-2032.
10. I. Tvaroška, Carbohydr. Res. 2004, 339, 1007-1014
11. I. Tvaroska, in Molecular modeling of retaining glycosyltransferases, Vol. 930 (Eds.:, J. F. G. Vliegenthart, R. J. Woods,), American Chemical Society, Washington, 2006, pp. 285-301.
12. C. Goedl and B. Nidetzky, ChemBioChem 2009, 10, 2333-2337.
13. J. C. Errey, S. S. Lee, R. P. Gibson, C. Martinez Fleites, C. S. Barry, P. M. Jung, A. C. O'Sullivan, B. G. Davis, G. J. Davies, Angew. Chem. 2010, 122, 1256-1259
14. Angew. Chem. Int. Ed. 2010, 49, 1234-1237.
15. S. S. Lee, S. Y. Hong, J. C. Errey, A. Izumi, G. J. Davies, B. G. Davis, Nat. Chem. Biol. 2011, DOI:.
16. A. Warshel, M. Levitt, J. Mol. Biol. 1976, 103, 227-249.
17. A. Laio, M. Parrinello, Proc. Natl. Acad. Sci. USA 2002, 99, 12562-12566.
18. M. Boero, T. Ikeda, E. Ito, K. Terakura, J. Am. Chem. Soc. 2006, 128, 16798-16807
19. V. Leone, F. Marinelli, P. Carloni, M. Parrinello, Curr. Opin. Struct. Biol. 2010, 20, 148-154.
20. L. Petersen, A. Ardevol, C. Rovira, P. J. Reilly, J. Phys. Chem. B 2009, 113, 7331-7339
21. L. Petersen, A. Ardevol, C. Rovira, P. J. Reilly, J. Am. Chem. Soc. 2010, 132, 8291-8300
22. I. J. Barker, L. Petersen, P. J. Reilly, J. Phys. Chem. B 2010, 114, 15389-15393.
23. W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graph. 1996, 14, 33-38.
24. H. S. Seo, Y. J. Koo, J. Y. Lim, J. T. Song, C. H. Kim, J. K. Kim, J. S. Lee, Y. D. Choi, Appl. Environ. Microbiol. 2000, 66, 2484-2490.
25. K. Fukui, Acc. Chem. Res. 1981, 14, 363-368.
26. A. Laio, J. VandeVondele, U. Rothlisberger, J. Chem. Phys. 2002, 116, 6941-6947.
27. R. Car, M. Parrinello, Phys. Rev. Lett. 1985, 55, 2471-2474.
28. Y. K. Zhang, T. S. Lee, W. T. Yang, J. Chem. Phys. 1999, 110, 46-54.
29. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
30. X. Biarnes, J. Nieto, A. Planas, C. Rovira, J. Biol. Chem. 2006, 281, 1432-1441.