Imine exchange in O-aryl and O-alkyl oximes as a base reaction for aqueous 'dynamic' combinatorial libraries. A kinetic and thermodynamic study

Journal of Physical Organic Chemistry

Volumn 12, Issue 5, 1999, Pages 357-363

  Polyakov, Vladimir A ^a,b   Nelen, Marina I ^a   Nazarpack Kandlousy, Noureddin ^a   Ryabov, Alexander D ^a,c   Eliseev, Alexey V ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Aqueous 'dynamic' combinatorial libraries; Imine exchange; Kinetics; Oximes; Thermodynamics

Indexed keywords

EID: 0000287934     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199905)12:5<357::AID-POC129>3.0.CO;2-Y     Document Type: Article

References (28)

1. For recent reviews on combinatorial chemistry see: (a) L. A. Thompson and J. A. Ellman. Chem. Rev. 96, 555-600 (1996) (b) X. Williard, I. Pop. L. Bourel, D. Horvath, R. Baudelle, P. MeInyk, B. Deprez and A. Tartar, Eur. J. Med. Chem. 31, 87-98 (1996) (c) F. Balkenhohol, C. von dem Bussche-Hünnefeld. A. Lansky and C. Zechel. Angew. Chem. Int. Ed. Engl. 35, 2288-2337 (1996).
2. For recent reviews on combinatorial chemistry see: (a) L. A. Thompson and J. A. Ellman. Chem. Rev. 96, 555-600 (1996) (b) X. Williard, I. Pop. L. Bourel, D. Horvath, R. Baudelle, P. MeInyk, B. Deprez and A. Tartar, Eur. J. Med. Chem. 31, 87-98 (1996) (c) F. Balkenhohol, C. von dem Bussche-Hünnefeld. A. Lansky and C. Zechel. Angew. Chem. Int. Ed. Engl. 35, 2288-2337 (1996).
3. For recent reviews on combinatorial chemistry see: (a) L. A. Thompson and J. A. Ellman. Chem. Rev. 96, 555-600 (1996) (b) X. Williard, I. Pop. L. Bourel, D. Horvath, R. Baudelle, P. MeInyk, B. Deprez and A. Tartar, Eur. J. Med. Chem. 31, 87-98 (1996) (c) F. Balkenhohol, C. von dem Bussche-Hünnefeld. A. Lansky and C. Zechel. Angew. Chem. Int. Ed. Engl. 35, 2288-2337 (1996).
4. P.G. Swann, R. A. Casanova, A. Desai, M. M. Frauenhoff, M. Urbancic, U. Slomczynska, A. J. Hopfinger, G. C. Le Breton and D. L. Venton, Biopolymers 40, 617-625 (1996).
5. (a) A. V. Eliseev and M. I. Nelen, J. Am. Chem. Soc. 119, 1147-1148 (1997)
6. (b) A. V. Eliseev and M. I. Nelen, Chem. Eur. J. 4, 825-834 (1998).
7. I. Huc and J.-M. Lehn. Proc. Natl. Acad. Sci. USA 94, 2106-2110 (1997).
8. (a) S. J. Rown and J. K. M. Sanders, Chem. Commun. 1407-1408 (1997)
9. (b) P. A. Brady and J. K. M. Sanders, J. Chem. Soc. Perkin Trans. I 3237-3253 (1997)
10. (c) P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev. 26, 327-336 (1997).
11. E. H. Cordes and W. P. Jencks. J. Am. Chem. Soc. 84, 832-837 (1962).
12. (a) W. P. Jencks, J. Am. Chem. Soc. 81, 475-781 (1959)
13. (b) T. K. Korpela and M. J. Mäkelä, Anal. Biochem. 110, 251-257 (1981).
14. (a) B. M. Anderson and W. P. Jencks, J. Am. Chem. Soc. 82, 1773-1777 (1960)
15. (b) E. H. Cordes and W.P. Jencks, J. Am. Chem. Soc. 84, 826-831 (1962).
16. (a) K. Koehler, W. Sandstrom and E. H. Cordes, J. Am. Chem. Soc. 86, 2431-2419 (1964)
17. (b) L. do Amaral, W. A. Sandstrom and E. H. Cordes, J. Am. Chem. Soc. 88, 2225-2233 (1966)
18. J. Mollin, F. Kaspárek and J. Lasovsky, Chem. Zvesti 29, 39-43 (1975).
19. W.P. Jencks, Catalysis in Chemistry and Enzymology. McGraw. Hill, New York, (1969).
20. (a) J. van Dijk and J. M. A. Zwagemakers, J. Med. Chem. 20, 1199-1206 (1977)
21. (b) A. Niwa, H. Iwamura, Y. Nakagawa and T. Fujita, J. Agric. Food Chem. 38, 514-520 (1990)
22. (c) R. M. Khomutov, T. Hyvönen, E. Karvonen, L. Kauppinen, T. Paalenen, L. Paulin, T. Eloranta, R.-L. Pajula, L.C. Andersson and H. Pösö, Biochem. Biophys. Res. Commun. 130, 596-602 (1985)
23. (d) T. Hycvönen, L. Alakuijala, L. Andersson, A. R. Khomutv, R. M. Khomutov and T. O. Eloranta, J. Biol. Chem. 263, 11138-11144 (1988)
24. (e) L. Persson, A. R. Khomutov and R. M. Khomutov, and R. M. Khomutov, Biochem. J. 257, 929-931 (1989)
25. (f) R. Poulin, J. A. Secrist III and A. E. Pegg, Biochem. J. 263, 215-221 (1989)
26. (g) T. O. Eloranta, A. R. Khomutov, R. M. Khomutov and T. Hyvönen, J. Biochem. 108, 593-598 (1990).
27. A. Rougny and M. Daudon. Bull. Soc. Chim. Fr. 5-6. 833-838 (1976).
28. G. Balacco. J. Chem. Inf. Comput. Sci. 34, 1235-1241 (1994).