Reactivity of amino acid nucleoside phosphoramidates: A mechanistic quantum chemical study

Journal of Physical Chemistry A

Volumn 116, Issue 1, 2012, Pages 644-652

  Michielssens, Servaas ^a   Maiti, Munmun ^a   Maiti, Mohitosh ^a   Dyubankova, Natalia ^a   Herdewijn, Piet ^a   Ceulemans, Arnout ^b  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOMOLECULES; HYDROLYSIS; PROTONATION; QUANTUM CHEMISTRY; REACTION INTERMEDIATES;

CARBOXYL GROUPS; EXPERIMENTAL EVIDENCE; LEAVING GROUPS; NUCLEOBASES; PHOSPHORAMIDATES; PROTONATED; QUANTUM CHEMICAL ANALYSIS; QUANTUM CHEMICAL STUDIES; SIMPLIFIED MODELS; TRANSITION STATE;

CHEMICAL ANALYSIS;

EID: 84962339420     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp208795f     Document Type: Article

References (30)

1. McGuigan, C.; Tollerfield, S.; Riley, P. Nucleic Acids Res. 1989, 17, 6065-6075
2. Mehellou, Y.; Balzarini, J.; McGuigan, C. ChemMedChem 2009, 4, 1779-1791
3. Cahard, D.; McGuigan, C.; Balzarini, J. Mini-Rev. Med. Chem. 2004, 4, 371-381
4. Adelfinskaya, O.; Herdewijn, P. Angew. Chem., Int. Ed. 2007, 46, 4356-4358
5. Adelfinskaya, O.; Terrazas, M.; Froeyen, M.; Marliere, P.; Nauwelaerts, K.; Herdewijn, P. Nucleic Acids Res. 2007, 35, 5060-5072
6. Giraut, A.; Herdewijn, P. ChemBioChem 2010, 11, 1399-1403
7. Giraut, A.; ping Song, X.; Froeyen, M.; Marliere, P.; Herdewijn, P. Nucleic Acids Res. 2010, 38, 2541-2550
8. Zlatev, I.; Giraut, A.; Morvan, F.; Herdewijn, P.; Vasseur, J.-J. Bioorg. Med. Chem. 2009, 17, 7008-7014
9. Maiti, M.; Michielssens, S.; Dyubankova, N.; Maiti, M.; Lescrinier, E.; Ceulemans, A.; Herdewijn, P. Chem.-Eur. J. Submitted.
10. Michielssens, S.; Trung, N. T.; Froeyen, M.; Herdewijn, P.; Nguyen, M. T.; Ceulemans, A. Phys. Chem. Chem. Phys. 2009, 11, 7274-7285
11. Frisch, M. J. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
12. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics Modell. 1996, 14, 33-39
13. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
14. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571
15. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630-6636
16. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129
17. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158
18. Floris, F.; Tomasi, J. J. Comput. Chem. 1989, 10, 616-627
19. Floris, F.; Tomasi, J.; Ahuir, J. J. Comput. Chem. 1991, 12, 784-791
20. Pierotti, R. Chem. Rev. 1976, 76, 717-726
21. Andersson, M. P.; Uvdal, P. J. Phys. Chem. A 2005, 109, 2937-2941
22. Ho, J.; Coote, M. L. Theor. Chem. Acc. 2010, 125, 3-21
23. Kazimierczuk, Z.; Vilpo, J.; Seela, F. Helv. Chim. Acta 1992, 75, 2289-2297
24. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 2007, 127.
25. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 2007, 126, 111-119
26. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
27. Lonnberg, T.; Ora, M.; Lonnberg, H. Mini-Rev. Org. Chem. 2010, 7, 33-43
28. Chen, Z.; Tan, B.; Li, Y.; Zhao, Y.; Tong, Y.; Wang, J. J. Org. Chem. 2003, 68, 4052-4058
29. Tan, B.; Lee, M.; Cui, M.; Liu, T.; Chen, Z.; Li, Y.; Ju, Y.; Zhao, Y.; Chen, K.; Jiang, H. Comp. Theor. Chem. 2004, 672, 51-60
30. Li-Ming, Q.; Shu-Xia, C.; Xiao-Yang, Z.; Ruo-Yu, L.; Ji-Hong, L.; Jian-Sha, L.; Yu-Fen, Z. Chin. J. Chem. 2007, 25, 1559-1562