A general buffer-acid-catalyzed C-O cleavage reaction in the hydrolysis of phenyl N-(phenoxycarbonyl)sulfamate ester

Chemistry - A European Journal

Volumn 5, Issue 5, 1999, Pages 1526-1533

  Blans, Patrick ^a   Vigroux, Alain ^a  

^a UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

Acid base catalysis; Hydrolyses; Reaction mechanisms; Sulfamate esters; Zwitterionic intermediates

Indexed keywords

AMPHOLYTE; ESTER; HYDROXIDE; PHENYL N (PHENOXYCARBONYL)SULFAMATE ESTER; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; HYDROLYSIS; MOLECULAR INTERACTION; PH MEASUREMENT; REACTION ANALYSIS; REACTION TIME;

EID: 0032958180     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990503)5:5<1526::AID-CHEM1526>3.0.CO;2-L     Document Type: Article

References (41)

1. M. J. Camarasa, P. Fernandez-Resa, M. T. Garcia-Lopez, F. G. de las Heras, P. P. Mendez-Castrillon, B. Alarcon, L. Carrasco, J. Med. Chem. 1985, 28, 40.
2. B. Alarcon, M. E. Gonzalez, L. Carrasco, P. P. Mendez-Castrillon, M. T. Garcia-Lopez, F. G. de las Heras, Antimicrob. Agents Chemother. 1988, 32, 1257.
3. M. J. Pérez-Pérez, J. Balzarini, E. de Clercq, M. J. Camarasa, Bioorg. Med. Chem. 1993, 1, 279.
4. P. Paul, T. M. Lutz, C. Osborn, S. Kyosseva, A. D. Elbein, H. Towbin, A. Radominska, R. R. Drake, J. Biol. Chem. 1993, 268, 12933; A. Radominska, P. Paul, S. Treat, H. Towbin, C. Pratt, J. Little, J. Magdalou, R. Lester, R. R. Drake, Biochim. Biophys. Acta 1994, 1205, 336; B. C. R. Zhu, R. R. Drake, H. Schweingruber, R. A. Laine, Arch. Biochem. Biophys. 1995, 319, 355.
5. P. Paul, T. M. Lutz, C. Osborn, S. Kyosseva, A. D. Elbein, H. Towbin, A. Radominska, R. R. Drake, J. Biol. Chem. 1993, 268, 12933; A. Radominska, P. Paul, S. Treat, H. Towbin, C. Pratt, J. Little, J. Magdalou, R. Lester, R. R. Drake, Biochim. Biophys. Acta 1994, 1205, 336; B. C. R. Zhu, R. R. Drake, H. Schweingruber, R. A. Laine, Arch. Biochem. Biophys. 1995, 319, 355.
6. P. Paul, T. M. Lutz, C. Osborn, S. Kyosseva, A. D. Elbein, H. Towbin, A. Radominska, R. R. Drake, J. Biol. Chem. 1993, 268, 12933; A. Radominska, P. Paul, S. Treat, H. Towbin, C. Pratt, J. Little, J. Magdalou, R. Lester, R. R. Drake, Biochim. Biophys. Acta 1994, 1205, 336; B. C. R. Zhu, R. R. Drake, H. Schweingruber, R. A. Laine, Arch. Biochem. Biophys. 1995, 319, 355.
7. L. W. L. Woo, A. Purohit, M. J. Reed, V. L. Potter, Bioorg. Med. Chem. Lett. 1997, 7, 3075.
8. D. R. Sliskovic, B. R. Krause, J. A. Picard, M. Anderson, R. F. Bousley, K. L. Hamelehle, R. Homan, T. N. Julian, Z. A. Rashidbaigi, R. L. Stanfield, J. Med. Chem. 1994, 37, 560; J. A. Picard, P. M. O'Brien, D. R. Sliskovic, M. Anderson, R. F. Bousley, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1996, 39, 1243; H. T. Lee, D. R. Sliskovic, J. A. Picard, B. D. Roth, W. Wierenga, J. L. Hicks, R. F. Bousley, K. L. Hamelehle, R. Homan, C. Speyer, R. L. Stanfield, B. R. Krause, J. Med. Chem. 1996, 39, 5031.
9. D. R. Sliskovic, B. R. Krause, J. A. Picard, M. Anderson, R. F. Bousley, K. L. Hamelehle, R. Homan, T. N. Julian, Z. A. Rashidbaigi, R. L. Stanfield, J. Med. Chem. 1994, 37, 560; J. A. Picard, P. M. O'Brien, D. R. Sliskovic, M. Anderson, R. F. Bousley, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1996, 39, 1243; H. T. Lee, D. R. Sliskovic, J. A. Picard, B. D. Roth, W. Wierenga, J. L. Hicks, R. F. Bousley, K. L. Hamelehle, R. Homan, C. Speyer, R. L. Stanfield, B. R. Krause, J. Med. Chem. 1996, 39, 5031.
10. D. R. Sliskovic, B. R. Krause, J. A. Picard, M. Anderson, R. F. Bousley, K. L. Hamelehle, R. Homan, T. N. Julian, Z. A. Rashidbaigi, R. L. Stanfield, J. Med. Chem. 1994, 37, 560; J. A. Picard, P. M. O'Brien, D. R. Sliskovic, M. Anderson, R. F. Bousley, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1996, 39, 1243; H. T. Lee, D. R. Sliskovic, J. A. Picard, B. D. Roth, W. Wierenga, J. L. Hicks, R. F. Bousley, K. L. Hamelehle, R. Homan, C. Speyer, R. L. Stanfield, B. R. Krause, J. Med. Chem. 1996, 39, 5031.
11. A. Vigroux, M. Bergon, C. Bergonzi, P. Tisnès, J. Am. Chem. Soc. 1994, 116, 11787.
12. P. Blans, A. Vigroux, J. Am. Chem. Soc. 1998, 120, 9574.
13. For recent reviews on antisense oligonucleotides see: E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543 and A. de Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366.
14. For recent reviews on antisense oligonucleotides see: E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543 and A. de Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366.
15. a≈2.
16. 9 when the leaving group is p-nitrophenol. See: H. Al-Rawi, A. Williams, J. Am. Chem. Soc. 1977, 99, 2671; A. Williams, K. T. Douglas, J. Chem. Soc. Perkin Trans. 2 1974, 1727.
17. 9 when the leaving group is p-nitrophenol. See: H. Al-Rawi, A. Williams, J. Am. Chem. Soc. 1977, 99, 2671; A. Williams, K. T. Douglas, J. Chem. Soc. Perkin Trans. 2 1974, 1727.
18. -1 in Equation (2).
19. Except for the 2,4-dinitrophenyl ester; see ref. [8].
20. A is characterized by a zero intercept at 0% free acid in both cases.
21. The rate constant for catalysis by the proton falls ca. 0.7 log unit below the line containing the carboxylic acids; see Figure 3.
22. R. A. More O'Ferrall, J. Chem. Soc. B 1970, 274.
23. W. P. Jencks, Chem. Rev. 1985, 85, 511.
24. A. Williams, K. T. Douglas, Chem. Rev. 1975, 75, 627 and references therein; J. March, Advanced Organic Chemistry, 3rd ed., Wiley Interscience, New York, 1985, pp. 873-896; T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper-Collins, New York, 1987, pp. 591-595.
25. A. Williams, K. T. Douglas, Chem. Rev. 1975, 75, 627 and references therein; J. March, Advanced Organic Chemistry, 3rd ed., Wiley Interscience, New York, 1985, pp. 873-896; T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper-Collins, New York, 1987, pp. 591-595.
26. A. Williams, K. T. Douglas, Chem. Rev. 1975, 75, 627 and references therein; J. March, Advanced Organic Chemistry, 3rd ed., Wiley Interscience, New York, 1985, pp. 873-896; T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper-Collins, New York, 1987, pp. 591-595.
27. HA) and pH, then there should not be, in principle, restrictions for the existence at low pH of a general/specific acid catalysis for leaving-group expulsion from the anionic form of the substrate.
28. W. P. Jencks, Chem. Rev. 1972, 72, 705.
29. -1 at 25°C.
30. W. P. Jencks, Acc. Chem. Res. 1976, 9, 425.
31. W. P. Jencks, Ace. Chem. Res. 1980, 13, 161.
32. A. J. Kirby, A. G. Varvoglis, J. Am. Chem. Soc. 1967, 89, 415.
33. E. J. Fendler, J. H. Fendler, J. Org. Chem. 1968, 33, 3852.
34. ROH < ca. 8 for sulfates.
35. [25, 29] similar considerations then apply to factors that govern changes in mechanism in hydrolysis of sulfate monoesters in acid.
36. W. W. Butcher, F. H. Westheimer, J. Am. Chem. Soc. 1955, 77, 2420; C. A. Bunton, D. R. Llewellyn, K. G. Oldham, C. A. Vernon, J. Chem. Soc. 1958, 3574.
37. W. W. Butcher, F. H. Westheimer, J. Am. Chem. Soc. 1955, 77, 2420; C. A. Bunton, D. R. Llewellyn, K. G. Oldham, C. A. Vernon, J. Chem. Soc. 1958, 3574.
38. S. J. Benkovic, P. A. Benkovic, J. Am. Chem. Soc. 1966, 88, 5504; J. L. Kice, J. M. Anderson, J. Am. Chem. Soc. 1966, 88, 5242.
39. S. J. Benkovic, P. A. Benkovic, J. Am. Chem. Soc. 1966, 88, 5504; J. L. Kice, J. M. Anderson, J. Am. Chem. Soc. 1966, 88, 5242.
40. G. Lohaus, Chem. Ber. 1972, 105, 2791.
41. No correction was applied for the small error incurred in reading pH values between pH 0 and 1.