The mechanistic and evolutionary basis of stereospecificity for hydrogen transfers in enzyme-catalysed processes

(Note: The full text of this document is currently only available in the PDF Version )

Kevin A. Reynolds and Koren A. Holland


Abstract

The original of stereospecificity in enzylme-catalysed processes is attributed to either mechanistic imperatives or to the evolutionary origin of an enzyme. Recent analysis of the synanti dichotomy for hydratase–dehydratase enzymes has clearly demonstrated that it is a historical contingency that has played a significant role in determination of stereospecificity. Historical contingencies also appear to play a significant role in (a) the selection of one out of a possible eight different stereochemical courses available for an enoyl thioester reductase, and (b) the discrimination between diastereotopic hydrogens in coenzyme B12-dependent rearrangements.


References

  1. H. F. Fisher, P. Ofner, E. E. Conn, B. Vennesland and F. Westheimer, J. Biol. Chem., 1953, 202, 687 Search PubMed.
  2. E. G. Weinhold, A. Glasfield, A. D. Ellington and S. A. Benner, Proc. Natl. Acad. Sci. USA, 1991, 88, 8420 Search PubMed.
  3. K. R. Hanson and I. A. Rose, Acc. Chem. Res., 1975, 8, 1 Search PubMed.
  4. S. A. Benner, Experientia, 1982, 38, 633 Search PubMed.
  5. N. J. Oppenheimer, J. Am. Chem. Soc., 1984, 106, 3032 Search PubMed.
  6. A. Glasfield, G. F. Leanz and S. A. Benner, J. Biol. Chem., 1990, 268, 11692 Search PubMed.
  7. R. Bentley, in Molecular Asymetry in Biology, ed. R. Bentley, Academic, New York, 1970, vol. 2, p. 1. Search PubMed.
  8. R. L. Dorit, L. Schoenbach and W. Gilbert, Science, 1990, 250, 1377 Search PubMed.
  9. C. R. Goward and D. J. Nicholls, Protein Science, 1994, 3, 1883 Search PubMed.
  10. J. R. Mohrig, K. A. Moerke, D. L. Cloutier, B. D. Lane, E. C. Person and T. B. Onasch, Science, 1995, 269, 527 Search PubMed.
  11. J. A. Gerlt and P. G. Gassman, J. Am. Chem. Soc., 1992, 114, 5928 Search PubMed.
  12. A. Scheneier, J. Harris, C. Kleanthous, J. R. Coggins, A. R. Hawkins and C. Abell, Bioorg. Med. Chem. Letts., 1993, 3, 1399 Search PubMed.
  13. J. R. Bottomley, A. R. Hawkins and C. Kleanthous, Biochem. J., 1996, 319, 269 Search PubMed.
  14. H. Liu, K. K. Wallace and K. A. Reynolds, J. Am. Chem. Soc., 1997, 119, 2973 Search PubMed.
  15. V. E. Anderson and G. G. Hammes, Biochemistry, 1984, 23, 2088 Search PubMed.
  16. H. Bergler, P. Wallner, A. Ebeling, B. Leitinger, S. Fuchsbichler, H. Aschauer, G. Kollenz, G. Hogenauer and F. Turnowskey, J. Biol. Chem., 1994, 86, 4387 Search PubMed.
  17. G. Meuer, G. Biermann, A. Schutz, S. Harth and E. Schweizer, Mol. Gen. Genet., 1992, 232, 106 Search PubMed.
  18. M. C. O'Sullivan, J. Schwab, T. M. Zabriskie, G. L. Helms and J. C. Vederas, J. Am. Chem. Soc., 1991, 113, 3997 Search PubMed.
  19. S. Chang and G. G. Hammes, Proc. Natl. Acad. Sci. USA., 1989, 86, 8373 Search PubMed.
  20. P. Wang, C. D. Denoya, M. R. Morgenstern, D. D. Skinner, K. K. Wallace, R. DiGate, N. Banavali, G. Schular, M. K. Speedie and K. A. Reynolds, J. Bacteriol., 1996, 178, 6873 Search PubMed.
  21. K. Arai, B. J. Rawlings, Y. Yoshizawa and J. C. Vederas, J. Am. Chem. Soc., 1989, 111, 3391 Search PubMed.
  22. C. M. H. Wantanabe, D. Wilson, J. E. Linz and C. A. Townsend, Chem. Biol., 1996, 3, 463 Search PubMed.
  23. B. S. Moore, H. Cho, R. Casati, E. Kennedy, K. A. Reynolds, J. M. Beale and H. G. Floss, J. Am. Chem. Soc., 1993, 115, 5254 Search PubMed.
  24. K. K. Wallace, K. A. Reynolds, K. Koch, H. A. I. McArthur, R. Wax and B. S. Moore, J. Am. Chem. Soc., 1994, 116, 11600 Search PubMed.
  25. E. N. G. Marsh, BioEssays, 1995, 17, 5 Search PubMed.
  26. W. Buckel and B. Golding, Chem. Soc. Rev., 1996, 25, 329 Search PubMed.
  27. A. Birch, A. Leistner and J. A. Robinson, J. Bacteriol., 1993, 175, 3511 Search PubMed.
  28. B. Beatrix, O. Zelder, D. Liner and W. Buckel, Eur. J. Biochem., 1994, 221, 101 Search PubMed.
  29. K. Wolfe, M. Michenfelder, A. Konig, W. E. Hull and J. Retey, Eur. J. Biochem., 1986, 156, 545 Search PubMed.
  30. G. Hartrampf and W. Buckel, FEBS Lett., 1984, 171, 73 Search PubMed.
  31. L. V. Chistoserdova and M. E. Lidstrom, Microbiol., 1996, 142, 1459 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.