Cleavage of Menger's aliphatic amide: A model for peptidase enzyme solely explained by proximity orientation in intramolecular proton transfer

Journal of Molecular Structure: THEOCHEM

Volumn 910, Issue 1-3, 2009, Pages 27-33

  Karaman, Rafik ^a  

^a AL QUDS UNIVERSITY   (Palestine)

Author keywords

Ab initio and DFT calculations; Amidase enzymes; Cleavage of aliphatic amides; Enzymes models; Proton transfer reactions

Indexed keywords

EID: 68049127782     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.06.011     Document Type: Article

References (64)

1. Bender M.L. Mechanism of Homogeneous Catalysis from Protons to Proteins (1971), Wiley Interscience, New York
2. Nelson D.L., and Cox M.M. Lehninger Principles of Biochemistry (2003), Worth Publishers, New York
3. Fersht A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding (1999), W.H. Freeman and Company, New York
4. Pascal R. Eur. J. Org. Chem. (2003) 1813
5. Pascal R. Bioorg. Chem. 31 (2003) 485
6. Smith R.M., and Hansen D.E. J. Am. Chem. Soc. 120 (1998) 8910
7. Radzicka A., and Wolfenden R. J. Am. Chem. Soc. 118 (1996) 6105
8. For a review in this topic, see. Czarink A.W. In: Liebman J.F., and Greenberg A. (Eds). Mechanistic Principles of Enzyme Activity (1988), VCH publishers, New York, NY
9. Bender M.L. J. Am. Chem. Soc. 79 (1957) 1258
10. Kluger R., Chin J., and Choy W.W. J. Am. Chem. Soc. 101 (1979) 6976
11. Groves J.T., and Dias R.M. J. Am. Chem. Soc. 101 (1979) 1033
12. Suh J., Kim M.J., and Seong N.J. J. Org. Chem. 46 (1981) 4354
13. Blagoeva I.B., and Kirby A.J. J. Chem. Soc. Perkin Trans. 2 (1985) 1017
14. Menger F.M., and Ladika M. J. Org. Chem. 35 (1990) 3006
15. Menger F.M., and Ladika M. J. Am Chem. Soc. 110 (1988) 6794
16. Menger F.M. Acc. Chem. Res. 18 (1985) 128
17. Menger F.M., Chow J.F., Kaiserman H., and Vasquez P.C. J. Am. Chem. Soc. 105 (1983) 4996
18. Menger F.M. Tetrahedron 39 (1983) 1013
19. Menger F.M., Grossman J., and Liotta D.C. J. Org. Chem. 48 (1983) 905
20. Menger F.M., Galloway A.L., and Musaev D.G. Chem. Commun. (2003) 2370
21. Menger F.M. Pure Appl. Chem. 77 (2005) 1873
22. R. Karaman, Presented in part at the 1st International Conference on Drug Design and Discovery in Dubai, UAE, February 4-7, 2008.
23. Karaman R. Tetrahedron Lett. 49 (2008) 5998
24. Karaman R. Bioorg. Chem. 37 (2009) 11
25. Karaman R. Tetrahedron Lett. 50 (2009) 452
26. R. Karaman, Res. Lett. Org. Chem., doi: 10.1155/2009/240253.
27. R. Karaman, Bioorg.Chem., doi: 10.1016/j.bioorg.2009.04.003.
28. R. Karaman, J. Phys. Chem., submitted for publication.
29. For reviews, see. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735
30. Milstein S., and Cohen L.A. J. Am. Chem. Soc. 92 (1970) 4377
31. Milstein S., and Cohen L.A. Proc. Natl. Acad. Sci. USA 67 (1970) 1143
32. Milstein S., and Cohen L.A. J. Am. Chem. Soc. 94 (1972) 9158
33. Bruice T.C., and Lightstone F.L. Acc. Chem. Res. 32 (1999) 127
34. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 119 (1997) 9103
35. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 118 (1996) 2595
36. Lightstone F.L., and Bruice T.C. J. Am. Chem. Soc. 116 (1994) 10789
37. Bruice T.C., and Bradbury W.C. J. Am. Chem. Soc. 90 (1968) 3803
38. Bruice T.C., and Bradbury W.C. J. Am. Chem. Soc. 87 (1965) 4846
39. Bruice T.C., and Pandit U.K. J. Am. Chem. Soc. 82 (1960) 5858
40. Bruice T.C., and Pandit U.K. Proc. Natl. Acad. Sci. USA 46 (1960) 402
41. Brown R.F., and Norman M.V.-G. J. Org. Chem. 21 (1956) 1046
42. Galli C., and Mandolini L. Eur. J. Org. Chem. (2000) 3117
43. Gerschler J.J., Wier K.A., and Hansen D.E. J. Org. Chem. 72 (2007) 654
44. Curran T.P., Borysenko C.W., Abelleira S.M., and Messier R.J. J. Org. Chem. 39 (1994) 3522
45. Dougan M.L., Chin J.L., Solt K., and Hansen D.E. Med. Chem. Lett. 14 (2004) 4153
46. Available from: .
47. Burker U., and Allinger N.L. Molecular Mechanics (1982), American Chemical Society, Washington, DC
48. Casewit C.J., Colwell K.S., and Rappe' A.K. J. Am. Chem. Soc. 114 (1992) 10024
49. Casewit C.J., Colwell K.S., and Rappe' A.K. J. Am. Chem. Soc. 114 (1992) 10035
50. Casewit C.J., Colwell K.S., and Rappe' A.K. J. Am. Chem. Soc. 114 (1992) 10046
51. Rappe' A.K., and Goddard W.A. J. Phys. Chem. 95 (1991) 3358
52. Rappe' A.K., Colwell K.S., and Casewit C.J. Inorg. Chem. 32 (1993) 3438
53. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902
54. Murrell J.N., and Laidler K.J. Trans. Faraday Soc. 64 (1968) 371
55. Available from: .
56. Muller K. Angew. Chem. Int. Ed. Engl. 19 (1980) 1
57. Dewar M.J.S., and Kirschner S. J. Am. Chem. Soc. 93 (1971) 4290
58. Karaman R., Huang J.-T.L., and Fry J.L. J. Comp. Chem. 11 (1990) 1009
59. Karaman R., Huang J.-T.L., and Fry J.L. J. Comp. Chem. 12 (1991) 536 and references therein
60. Cancès M.T., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
61. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
62. Mennucci B., Cancès M.T., and Tomasi J. J. Phys. Chem. B 101 (1997) 10506
63. Tomasi J., Mennucci B., and Cancès M.T. J. Mol. Struct. (THEOCHEM) 464 (1997) 211
64. Scheiner S. J. Am. Chem. Soc. 103 (1981) 315