Optimal environment for maximal molecular recognition against temperature. Three distinct patterns in temperature-recognition profiles as a function of composition of aqueous binary solvents

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 12, 2004, Pages 2213-2218

  Endo, Tadashi ^a   Sugio, Keitaro ^a   Kogure, Sadahiro ^a   Horikosi, Suguru ^a   Tojima, Motohiro ^a   Aono, Yosihiro ^a   Ito, Masato M ^b  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

^b SOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYST SELECTIVITY; OXIDATION; THERMAL EFFECTS;

BINARY SOLVENTS; MAXIMAL MOLECULAR RECOGNITION; RECOGNITION SITES;

ORGANIC SOLVENTS;

DISULFIDE; SOLVENT; THIOL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BINDING SITE; CHEMICAL BINDING; CHEMICAL COMPOSITION; CHEMICAL REACTION; MOLECULAR RECOGNITION; OXIDATION; TEMPERATURE DEPENDENCE;

EID: 11144283075     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.2213     Document Type: Article

References (36)

1. For reviews on aqueous solutions, see: a) F. Franks and D. J. G. Ives, Q. Rev., 20, 1 (1966).
2. b) E. S. Amis and J. F. Hinton, "Solvent Effects on Chemical Phenomena," Academic Press, New York (1973), Vol. 1, Chap. 4.
3. c) M. C. R. Symons, Acc. Chem. Res., 14, 179 (1981).
4. d) R. W. Cargill, Chem. Soc. Rev., 1993, 135.
5. e) S. Taniewska-Osinska, Chem. Soc. Rev., 1993, 205.
6. f) W. E. Waghorne, Chem. Soc. Rev., 1993, 285.
7. D. Mirejovsky and E. M. Arnett, J. Am. Chem. Soc., 105. 1112 (1983).
8. "International Critical Tables of Numerical Data, Physics, Chemistry and Technology," ed by E. W. Washburn, McGraw-Hill, New York (1929), Vol. V, pp. 22-23; "Landolt-Börnstein Physikalisch-Chemische Tabellen," ed by W. A. Roth and K. Scheel, Springer, Berlin (1931), p. 106.
9. a) "International Critical Tables of Numerical Data, Physics, Chemistry and Technology," ed by E. W. Washburn, McGraw-Hill, New York (1929), Vol. V, pp. 22-23; "Landolt-Börnstein Physikalisch-Chemische Tabellen," ed by W. A. Roth and K. Scheel, Springer, Berlin (1931), p. 106.
10. b) G. S. Beddard, T. Doust, and J. Hudales, Nature, 294, 145 (1981).
11. G. Némethy and H. A. Scheraga, J. Chem. Phys., 36, 3401 (1962).
12. In this connection, significant problems remain to be resolved: why living systems utilize these three branched alkyl groups (isopropyl, isobutyl, and s-butyl ones) among only twenty repertories, but not straight-chain ones (i.e., propyl and butyl ones) [H. Neurath and R. L. Hill, "The Proteins," 3rd ed. Academic Press, New York (1979), Vol. IV, pp. 11-15].
13. T. Endo, A. Kuwahara, H. Tasai, T. Murata, M. Hashimoto, and T. Ishigami, Nature, 268, 74 (1977).
14. T. Endo, H. Takei, T. Isago, J. Kato, M. M. Ito, K. Guro, K. Akiyama, Y. Nakajima, and H. Kataoka, J. Am. Chem. Soc. 111, 8166 (1989).
15. a) T. Endo, Y. Takeda, T. Orii, Y. Kaneko, and M. Kondo, Chem. Lett., 1979, 1455.
16. b) A. Uchida, Y. Ohashi, Y. Sasada, Y. Kaneko, and T. Endo, Acta Crystallogr., C40, 115 (1984).
17. Seeman et al. reported that using two hydrogen bonds, fidelity of base pair recognition might be achieved, whereas a single hydrogen bond was inadequate for uniquely identifying any particular base pair: N. C. Seeman, J. M. Rosenberg, and A. Rich, Proc. Natl. Acad. Sci. U.S.A., 73, 804 (1976).
18. a) T. Endo, M. M. Ito, Y. Yamada, H. Saito, K. Miyazawa, and M. Nishio, J. Chem. Soc., Chem. Commun., 1983, 1430.
19. b) M. M. Ito, J. Kato, S. Takagi, E. Nakashiro, T. Sato, Y. Yamada, H. Saito, T. Namiki, I. Takamura, K. Wakatsuki, T. Suzuki, and T. Endo, J. Am. Chem. Soc., 110, 5147 (1988).
20. a) T. Endo, H. Tasai, K. Miyazawa, M. Endo, K. Kato, A. Uchida, Y. Ohashi, and Y. Sasada, J. Chem. Soc., Chem. Commun., 1983, 636.
21. b) T. Endo, Top. Curr. Chem., 128, 91 (1985).
22. T. Endo, K. Tajima, M. Yamashita, M. M. Ito, J. Nishida, and T. Ogikubo, J. Chem. Soc., Chem. Commun., 1986, 1561.
23. The oxidation was chosen as a model reaction, since the correct pairing of half-cystine residues (specific S-S bond formation) has been suggested to depend upon specific noncovalent bonds: C. B. Anfinsen, M. Sela, and J. P. Cooke, J. Biol. Chem., 237, 1825 (1962).
24. T. Endo, A. Okubo, Y. Kaneko, M. Uehara, H. Tasai, A. Sato, K. Nikki, N. Nakagawa, and S. Kamei, Bull. Chem. Soc. Jpn., 55, 2224 (1982).
25. N. Nakagawa, K. Nikki, M. M. Ito, J. Kato, H. Ota, M. Ogino, A. Miyoshi, and T. Endo, Chem. Lett., 1990, 1959.
26. The large reactivity difference between thiols 1 and 2 is not responsible for the observed selectivity. This is because r values should become negative regardless of the reaction systems employed, if the selectivity depends upon the reactivity difference; however, the r gives positive values for almost all reaction systems (Figs. 1-3, 5, and 6).
27. For reviews and books on hydrophobic interaction, see: a) W. P. Jencks, "Catalysis in Chemistry and Enzymology," McGraw-Hill, New York (1969), Chap. 8.
28. b) C. Tanford, "The Hydrophobic Effect," 2nd ed, Wiley, New York (1980).
29. c) A. Ben-Naim, "Hydrophobic Interactions," Plenum, New York (1980).
30. d) W. Blokzijl and J. B. F. N. Engberts, Angew. Chem., Int. Ed. Engl., 32, 1545 (1993).
31. Ref. 17c, Chap. 3.
32. G. Carthy, D. Feakins, and W. E. Waghorne, J. Chem. Soc., Faraday Trans, 1, 83, 2585 (1987).
33. J. Kato, M. M. Ito, K. Hagino, N. Naitoh, M. Misaka, E. Fujishiro, and T. Endo, Bull. Chem. Soc. Jpn., 61, 1419 (1988).
34. T. Endo, T. Ueda. T. Isago, J. Kato, T. Suzuki, M. Misaka, and M. M. Ito, Bull. Chem. Soc. Jpn., 60, 2298 (1987).
35. T. Endo, Y. Aono, T. Yazawa, M. Hayashi, Y. Yokose, T. Iida, and T. Isago, Bull. Chem. Soc. Jpn., 70, 3047 (1997).
36. T. Endo, H. Takei, T. Isago, K. Guro, Y. Nakajima, J. Kato, and M. M. Ito. J. Chem. Soc., Perkin Trans. 2, 1990, 1029.