Mechanism of SN2 disulfide bond cleavage by phosphorus nucleophiles. Implications for biochemical disulfide reducing agents

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8298-8307

  Dmitrenko, Olga ^a   Thorpe, Colin ^a   Bach, Robert D ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL DISULFIDE REDUCING AGENTS; PHOSPHORUS NUCLEOPHILES; SOLVENT CORRECTIONS; TRIMETHYLPHOSPINE (TMP);

ACTIVATION ENERGY; MOLECULAR STRUCTURE; NUCLEOPHILES; PHOSPHORUS; POSITIVE IONS; WATER;

CHEMICAL BONDS;

DIMETHYL DISULFIDE; DISULFIDE; PHOSPHINE DERIVATIVE; PHOSPHONIUM DERIVATIVE; PHOSPHORUS; REDUCING AGENT; THIOL DERIVATIVE; TRIMETHYLPHOSPHINE; UNCLASSIFIED DRUG; WATER; ORGANOPHOSPHATE; TRIMETHYL PHOSPHATE;

ARTICLE; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; DISULFIDE BOND; ENERGY TRANSFER; MOLECULAR DYNAMICS; MOLECULAR STABILITY; REACTION ANALYSIS; SOLVATION; CHEMICAL MODEL; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION;

DISULFIDES; KINETICS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PHOSPHORIC ACID ESTERS; REDUCING AGENTS;

EID: 35548957414     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071271w     Document Type: Article

References (66)

1. N2 Mechanism; Wiley: New York 1992.
2. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York 1987.
3. Parker, A. J.; Kharasch, N. Chem. Rev. 1959, 59, 583.
4. (a) Holmgren, A. Structure 1995, 3, 239.
5. (b) Darby, N. J.; Freedman, R. B.; Creighton, T. E. Biochemistry 1994, 33, 7937.
6. (c) Wood, Z. A.; Poole, L. B.; Karplus, P. A. Biochemistry 2001, 40, 3900.
7. (d) Chivers, P. T.; Prehoda, K. E.; Raines, R. T. Biochemistry 1997, 36, 4061.
8. (a) Gross, F.; Sevier, C. S.; Vala, A.; Kaiser, C. A.; Fass, D. Nature Struct. Biol. 2002, 9, 61.
9. (b) Ellgaard, L.; Ruddock, L. W. EMBO Rep. 2005, 6, 28.
10. (c) Sevier, C. S.; Kaiser, C. A. Antioxid Redox Signal 2006, 8, 797.
11. (d) Nakamoto, H.; Bardwell, J. C. Biochim. Biophys. Acta 2004, 1694, 111.
12. (e) Wilkinson, B.; Gilbert, H. F. Biochim. Biophys. Acta-Proteins Proteomics 2004, 1699, 35.
13. Keire, D. A.; Strauss, E.; Guo, W.; Noszal, B.; Rabenstein, D. L. J. Org. Chem. 1992, 57, 123.
14. (a) Overman, L. E.; Matzinge, D.; O'connor, E. M.; Overman, J. D. J. Am. Chem. Soc. 1974, 96, 6081.
15. (b) Overman, L. E.; Petty, S. T. J. Org. Chem. 1975, 40, 2779.
16. (c) Overman, L. E.; O'connor, E. M. J. Am. Chem. Soc. 1976, 98, 771.
17. (a) Houk, J.; Whitesides, G. M. J. Am. Chem. Soc. 1987, 109, 6825.
18. (b) Singh, R.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 1190.
19. (c) Singh, R.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 6304.
20. Schönberg, A. Chem. Ber. 1935, 68, 163.
21. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648.
22. (a) Han, J. C.; Han, G. Y. Anal. Biochem. 1994, 220, 5.
23. (b) Gray, W. R. Protein Sci. 1993, 2, 1732.
24. (c) Getz, E. B.; Xiao, M.; Chakrabarty, T.; Cooke, R.; Selvin, P. R. Anal. Biochem. 1999, 273, 73.
25. (d) Geiger, L. K.; Kortuem, K. R.; Alexejun, C.; Levin, L. A. Neuroscience 2002, 109, 635.
26. (e) de Lamirande, E.; Gagnon, C. Free Radical Biol. Med. 1998, 25, 803.
27. Cline, D. J.; Redding, S. E.; Brohawn, S. G.; Psathas, J. N.; Schneider, J. P.; Thorpe, C. Biochemistry 2004, 43, 15195.
28. (a) For earlier discussions concerning the nature of chemical bonding in hypervalent molecules, see: Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
29. (b) An excellent discussion of revised models for hypervalent bonding my be found in: Dobado, J. A.; Martinez-Garcia, H.; Molina, J. M.; Sundberg, M. R. J. Am. Chem. Soc. 1990, 120, 8461.
30. N2 attack at carbon versus silicon, see: Bento, A. P.; Sola, M.; Bickelhaupt, F. M. J. Comput. Chem. 2005, 26, 1497.
31. N2 attack at silicon see: Bento, A. P.; Bickelhaupt, F. M. J. Org. Chem. 2007, 72, 2201.
32. N2 attack at phosphorus see: van Bochove, M. A.; Swart, M.; Bickelhaupt, F. M. J. Am. Chem. Soc. 2006, 128, 10738.
33. (a) Bachrach, S. M.; Mulhearn, D. C. J. Phys. Chem. 1996, 100, 3535.
34. (b) Bachrach, S. M.; Hayes, J. M.; Dao, T.; Mynar, J. L. Theor. Chem. Ace 2002, 107, 266.
35. (c) Bachrach, S. M.; Pereverzev, A. Org. Biomol. Chem. 2005, 3, 2095.
36. (d) Hayes, J. M.; Bachrach, S. M. J. Phys. Chem. 2003, 107, 7952.
37. (e) Bachrach, S. M.; Chamberlin, A. C. J. Org. Chem. 2003, 68, 4743.
38. (f) Bachrach, S. M.; Gailbreath, B. D. J. Org. Chem. 2001, 66, 2005.
39. (a) Bach, R. D.; Dmitrenko, O.; Thorpe, C. J. Org. Chem. To be submitted,
40. (b) Glukhovtsev, M. N.; Bach, R. D.; Pross, A.; Radom, L. Chem. Phys. Lett. 1996, 160, 558.
41. (a) Frisch, M. J. et al. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
42. (b) Gaussian 03, revision B.05 (SGI64-G03RevB.05); Gaussian, Inc.: Pittsburgh, PA, 2003.
43. See the Supporting Information for the full list of authors, (c) Barone, V.; Cossi, M. J. Phys. Chem. A. 1998, 102, 1995.
44. (d) Barone, V.; Cossi, M.; Tomasi, J. J. Comp. Chem. 1998, 19, 404.
45. (a) Becke, A. D. Phys. Rev. A 1988, 37, 785.
46. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B41, 785.
47. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
48. (d) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 80, 11623.
49. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
50. (a) NBO Version 3.1, Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
51. (b) Carpenter, J. E.; Weinhold, F. THEOCHEM 1988, 169, 41.
52. (c) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
53. (d) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
54. (a) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764.
55. (b) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
56. Bach, R. D.; Thorpe, C.; Dmitrenko, O. J. Phys. Chem. A. 2002, 106, 4325.
57. (a) Milfeld, K.; Guiang, C.; Pamidighantam, S.; Giuliani, J. Proceedings of the Linux Clusters: The HPC Revolution,
58. (b) Dooley, R.; K. Milfeld, K.; Guiang, C.; Pamidighantam, S.; Allen, G. Proceedings of the Global Grid Forum 14, 2005.
59. (a) Bach, R. D.; Ayala, P. Y.; Schlegel, H. B. J. Am. Chem. Soc. 1996, 118, 12758.
60. (b) Bach, R. D.; Dmitrenko, O.; Estévez, C. M. J. Am. Chem. Soc. 2005, 127, 3140.
61. (c) Estevez, C. M.; Dmitrenko, O.; Winter, J. E.; Bach, R. D. J. Org. Chem. 2000, 65, 8629.
62. (d) Bach, R. D.; Dmitrenko, O. J. Phys. Chem. B 2003, 107, 12851.
63. Jursic, B. S. Int. J. Quant. Chem. 1997, 62, 291.
64. Price, C. C.; Oae, S. Sulfur Bonding: Ronald Press: New York, 1962.
65. (a) Henderson, W. A., Jr.; Streuli, C. A. J. Am. Chem. Soc. 1960, 82, 5791.
66. (b) Henderson, W. A., Jr.; Buckler, C. A. J. Am. Chem. Soc. 1960, 82, 5794.