Enzymatic and Nonenzymatic Reactions of Cyclic Sulfonate and Sulfate Esters

Accounts of Chemical Research

Volumn 3, Issue 5, 1970, Pages 145-151

  Kaiser, Emil Thomas ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001257855     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar50029a001     Document Type: Article

References (50)

1. E. T. Kaiser, I. R. Katz, and T. F. Wulfers, J. Amer. Chem. Soc., 87, 3781 (1965).
2. O. R. Zaborsky and E. T. Kaiser, J. Amer. Chem. Soc., 88, 3084 (1966).
3. E. T. Kaiser and O. R. Zaborsky, J. Amer. Chem. Soc., 89, 1393 (1967).
4. A review on the cyclio phosphate esters has appeared: F. H. Westheimer, Accounts Chem. Res., 1, 70 (1968).
5. P. C. Haake and F. H. Westheimer, J. Amer. Chem. Soc., 83, 1102 (1961).
6. C. A. Bunton, D. R. Llewellyn, K. G. Oldham, and C. A. Vernon, J. Chem. Soc., 3574 (1958).
7. E. T. Kaiser, M. Panar, and F. H. Westheimer, J. Amer. Chem. Soc., 85, 602 (1963).
8. E. T. Kaiser and K. Kudo, J. Amer. Chem. Soc., 89, 6725 (1967).
9. E. T. Kaiser and O. R. Zaborsky, J. Amer. Chem. Soc., 90, 4626 (1968).
10. P. S. Tobias and F. J. Kézdy, J. Amer. Chem. Soc., 91, 5171 (1969).
11. For a discussion of the methods employed, the reader is referred to P. Muller, D. F. Mayers, O. R. Zaborsky, and E. T. Kaiser, J. Amer. Chem. Soc., 91, 6732 (1969).
12. “Pentacoordinate” sulfur compounds were postulated as intermediates in organic reactions in a paper by B. M. Trost, R. LaRochelle, and R. C. Atkins, J. Amer. Chem. Soc., 91, 2975 (1969). Also, a test for pseudorotation in “pentacoordinate” sulfur compounds has been described by
13. R. Tang and K. Mislow, J. Amer. Chem. Soc., 91, 5644 (1969). However, in these instances, the term “pentacoordinate” was employed to describe sulfur compounds of the type RiS: where the lone pair of electrons was included as a ligand. There is a clear distinction between such “pentacoordinate” intermediates and the ones like 1, 0 which are discussed in this review.
14. F. P. Boer, J. J. Flynn, E. T. Kaiser, O. R. Zaborsky, D. A. Tomalia, A. E. Young, and Y. C. Tong, J. Amer. Chem. Soc., 90, 2970 (1968);
15. F. P. Boer and J. J. Flynn, J. Amer. Chem. Soc., 91, 6604 (1969);
16. E. B. Fleischer, E. T. Kaiser, P. Langford, S. Hawkinson, A. Stone, and R. Dewar, Chem. Commun., 197 (1967).
17. K. W. Lo, K. Kudo, W. Berg, and E. T. Kaiser, manuscript in preparation.
18. T. C. Bruice and S. Benkovic, “Bioorganic Mechanisms,” Vol. 1, W. A. Benjamin, Inc., New York, N. Y., 1966, pp 46-66.
19. J. H. Heidema and E. T. Kaiser, manuscript in preparation.
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30. J. H. Heidema and E. T. Kaiser, J. Amer. Chem. Soc., 90, 1860 (1968);
31. J. H. Heidema, Ph. D. Thesis, Department of Chemistry, University of Chicago, 1969.
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41. For a study of a related phenomenon in aminothiol compounds, see R. E. Benesch and R. Benesch, J. Amer. Chem. Soc., 77, 5877 (1955).
42. P. Tobias, J. H. Heidema, K. W. Lo, E. T. Kaiser, and F. J. Kézdy, J. Amer. Chem. Soc., 91, 202 (1969).
43. A computer program written by Dr. P. L. Hall was used. See P. L. Hall, Ph. D. Thesis, University of Chicago, 1967.
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45. E. T. Kaiser and K. W. Lo, J. Amer. Chem. Soc., 91, 4912 (1969).
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48. Y. Pocker and J. T. Stone, Biochemistry, 6, 668 (1967).
49. The use of the sultone 12 as an active-site titrant has been described: J. H. Heidema and E. T. Kaiser, Chem. Commun., 300 (1968);
50. F. J. Kézdy and E. T. Kaiser, “Principles of Active Site Titration of Proteolytic Enzymes,” a review which will appear in a forthcoming volume of Methods Enzymol.