Observation of an Intimate Ion Pair Intermediate in the Ionization of Thio Addition Products of NAD(P)+ Analogues. Implications for 3-Phosphoglyceraldehyde Dehydrogenase

Journal of the American Chemical Society

Volumn 106, Issue 20, 1984, Pages 6029-6037

  van Keulen, B J ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845470489     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00332a047     Document Type: Article

References (37)

1. Wallenfels, Κ.; Schüly, H. Justus Liebigs Ann. Chem. 1959, 621, 86.
2. Foster, R.; Fyfe, C. A. Tetrahedron 1969, 25, 1489.
3. Lindquist, R. N.; Cordes, E. H. J. Am. Chem. Soc. 1968, 90, 1269.
4. Lovesey, A. C. J. Med. Chem. 1969, 12, 1018.
5. Kaválek, J.; Lyčka, A.; Macháĉek, V.; Šterba, V. Collect. Czech. Chem. Commun. 1975, 40, 1932.
6. Wallenfels, Κ.; Hofmann, D.; Schüly, H. Justus Liebigs Ann. Chem. 1959, 621, 188.
7. Piepers, O.; Kellogg, R. M. J. Chem. Soc., Chem. Commun. 1980, 1147.
8. Kröhnke, E.; Ellegast, K.; Bertram, E.; Justus Liebigs Ann. Chem. 1956, 600, 176, 198.
9. Kröhnke, E.; Vogt, I. Justus Liebigs Ann. Chem. 1956, 600, 211.
10. Doering, W. V. E.; McEwen, W. E. J. Am. Chem. Soc. 1951, 73, 2104.
11. Wenkert, E.; Reynolds, G. D. Synth. Commun. 1973, 241.
12. Steglich, W.; Höfle, G. Chem. Ber. 1969, 102 1129.
13. Kaválek, J.; Lyčka, A.; Macháĉek, V.; Sterba, V. Collect. Czech. Chem. Commun. 1976, 41, 67.
14. Zoltewicz, J. A.; Helmick, L. S.; O'Halloran, J. K. J. Org. Chem. 1976, 41, 1308.
15. Wenkert, E.; Dave, K. G.; Haglid, F.; Lewis, R. G.; Oishi, T.; Stevens, R. V.; Terashima, M. J. Org. Chem. 1968, 33, 747.
16. Damji, S. W. H.; Fyfe, C. A. J. Org. Chem. 1979, 44, 1757.
17. Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1.
18. de Vries, J. G.; Kellogg, R. M.; J. Org. Chem. 1980, 45, 4126.
19. Krimsky, I.; Racker, E. Science (Washington, D.C.) 1955,122, 319.
20. Racker, E.; Krimsky, I. Nature (London) 1952, 169, 1043.
21. Herriott, J. R.; Camerman, A.; Deranleau, D. A. J. Am. Chem. Soc. 1974, 96, 1584.
22. Behr, J.-P.; Lehn, J. M. Helv. Chim. Acta 1980, 63, 2112.
23. Jouin, P.; Troostwijk, C. B.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 2091.
24. van Bergen, T. J.; Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1979, 44, 4953.
25. Nakamura, Κ.; Yasui, S.; Ohno, A.; Oka, S. Tetrahedron Lett. 1983, 24, 2001.
26. van Bergen, T. J.; Mulder, T.; van der Veen, R. A.; Kellogg, R. M.; Tetrahedron 1978, 34, 2377.
27. van Bergen, T. J., Kellogg, R. M. J. Am. Chem. Soc. 1972, 94, 8451.
28. Farnum, D. G. Adv. Phys. Org. Chem. 1975, 11, 123.
29. Hogen-Esch, T. E.; Smid, J. J. Am. Chem. Soc. 1966, 88, 318.
30. Collins, G. L.; Smid, J. J. Am. Chem. Soc. 1973, 95,1503.
31. Smid, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 112.
32. Hogen-Esch, T. E. Adv. Phys. Org. Chem. 1977, 15, 153.
33. Sneen, R. A. Acc. Chem. Res. 1973, 6, 46.
34. Gordon, J. E. The Organic Chemistry of Electrolyte Solutions Olah, G. A., Ed.; Wiley-Interscience: New York 1975.
35. Feigel, M.; Kessler, H.; Walter, A. Chem. Ber. 1978, 111, 2947.
36. Kessler, H.; Walter, A. Angew. Chem., Int. Ed. Engl. 1973, 12, 773.
37. Harris, J. I.; Waters, M. The Enzymes 1976, 13, 1–49.