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The Nature of Molecular Recognition: Examples from Host/Guest Chemistry

  • P. A. Kollman
Chapter
Part of the NATO ASI Series book series (ASIC, volume 426)

Abstract

What is molecular recognition? It is the fact that molecular hosts bind more tightly to certain “guest” molecules than others. What is the physical basis for it? There are two possible sources for this — covalent, where certain guests have the appropriate groups to form stronger covalent chemical bonds with the host than do others; or non-covalent, where the stronger binding of certain guests to the host is due to a combination of electrostatic and van der Waals interactions between host and guest and differential internal strain. The focus on this review is mainly on our work in non-covalent molecular recognition of organic hosts by small neutral and ionic molecular guests from 1982-present. This enables us to give an historical perspective on the evolution of computational techniques as well as describing the increase in our understanding of molecular recognition.

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References

  1. (1).
    Weiner, P. and Kollman, P.A. J. Comp. Chenu 2, 287, (1981).CrossRefGoogle Scholar
  2. (2).
    Yamabe, T., Hori, K., Akayi, K. and Fukui, K. Tetrahedron 35, 1065, (1979).CrossRefGoogle Scholar
  3. (3).
    Wipff, G., Weiner, P. and Kollman, P. J. Amer. Chem. Soc. 104, 3249–3258 (1982).CrossRefGoogle Scholar
  4. (4).
    Weiner, P.K., Profeta, S., Jr., Wipff, G., Havel, T., Kuntz, I.D., Langridge, R. and Kollman, P.A. Tetrahedron 39, 1113–1121 (1983).CrossRefGoogle Scholar
  5. (5).
    Wipff, G. and Kollman, P. Nour. J. Chemie 9, 457 (1985).Google Scholar
  6. (6).
    Cram, D.J., Lein, G.M., Kaneda, T., Helgeson, R.C., Knoller, C.B., Maverick, E. and Trueblood, K.N. J. Amer. Chem. Soc. 103, 6228 (1981).CrossRefGoogle Scholar
  7. (7).
    Kollman, P.A., Wipff, G. and Singh, U.C. J. Amer. Chem. Soc. 107, 2219–2219 (1985).CrossRefGoogle Scholar
  8. (8).
    Ranghino, G., Romano, S., Lehn, J.M. and Wipff, G. J. Amer. Chem. Soc. 107, 7873–7877 (1985).CrossRefGoogle Scholar
  9. (9).
    Lybrand, T.P., McCammon, J.A., Wipff, G. Proc. Nat. Acad. Sci. 83, 833 (1986).CrossRefGoogle Scholar
  10. (10).
    Grootenhuis, P.D.J. and Kollman, P.A. J. Amer. Chem. Soc. 111, 2152–2158 (1989).CrossRefGoogle Scholar
  11. (11).
    Lopez, M.A. and Kollman, P.A. J. Amer. Chem. Soc. 111, 6212–6222 (1989).CrossRefGoogle Scholar
  12. (12).
    Grootenhuis, P.D.J. and Kollman, P.A. J. Amer. Chem. Soc. 111, 4046–4051 (1989).CrossRefGoogle Scholar
  13. (13).
    Miyamoto, S. and Kollman, P.A. J. Amer. Chem. Soc. 114, 3668–3674 (1992).CrossRefGoogle Scholar
  14. (13).
    Miyamoto, S. and Kollman, P.A. J. Amer. Chem. Soc. 114, 3668–3674 (1992).CrossRefGoogle Scholar
  15. (15).
    Jorgensen, W.L. and Buckner, K., 91, 6083 (1987).Google Scholar
  16. (16).
    Dang, L.X. and Kollman, P.A. J. Amer. Chem. Soc. 112, 5716–5720 (1990).CrossRefGoogle Scholar
  17. (17).
    Straatsma, T.P. and McCammon, J.A. J. Chem. Phys. 91, 3631–3637 (1989).CrossRefGoogle Scholar
  18. (18).
    Sun, Y. and Kollman, P. J. Comp. Chem. 13, 33–40 (1992)CrossRefGoogle Scholar
  19. (19).
    Sun, Y. and Kollman, P. J. Chem. Phys. 97, 5109–5112 (1992).Google Scholar
  20. (20).
    Sun, Y. and Kollman, P. (unpublished).Google Scholar
  21. (21).
    Bayly, C. and Kollman, P.A. “Molecular Dynamics and Free Energy Calculations on the Peculiar Bimodal Alkali Ion Selectivity of an 8-Subunit Covitand” J.Amer. Chem Soc. (submitted).Google Scholar
  22. (22).
    Thomas, B. and Kollman, P.A., manuscript in preparation.Google Scholar
  23. (23).
    Sun, Y., Caldwell, J.C. and Kollman, P.A., manuscript in preparation.Google Scholar
  24. (24).
    Warshel, A. “Computer Modeling of Chemical Reactions in Solution and in Enzymes”, Wiley-Interscience, New York, (1991); Field, M., Bash, P. and Karplus, J. J. Comp. Chem. 11, 700–733 (1990); Singh, U.C. and Kollman, P.A. J. Comp. Chem. 7, 718–730 (1986); Cramer, C.J. and Truhlar, D.G. Science 256, 213–217 (1992); Gao, J.L. and Xia, X. F. Science 258, 631–635 (1992).Google Scholar
  25. (25).
    Honig, B., Sharp, K. and Yang, A.S. J. Phys. Chem 97, 1101 (1993).CrossRefGoogle Scholar
  26. (26).
    Still, W.C., Tempczyk, A., Hawley, R.C., Henderson, T. J. Amer. Chem. Soc. 112, 6127–6129 (1990).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1994

Authors and Affiliations

  • P. A. Kollman
    • 1
  1. 1.Department of Pharmaceutical ChemistryUniversity of CaliforniaSan FranciscoUSA

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