Biosynthesis of isoprenoids in Escherichia coli: stereochemistry of the reaction catalyzed by isopentenyl diphosphate:dimethylallyl diphosphate isomerase

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Aquiles E. Leyes, Jonathan A. Baker, Frederick M. Hahn and C. Dale Poulter


Abstract

The interconversion of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) catalyzed by E. coli and S. pombe IPP isomerase proceeds with removal of the pro-R proton at C2 of IPP and addition of a water-derived proton to the re face of the C2–C3 double bond in DMAPP; this is the same stereochemistry observed for S. cerevisiae and rat liver enzymes.


References

  1. K. Clifford, J. W. Cornforth, R. Mallaby and G. T. Phillips, J. Chem. Soc., Chem. Commun., 1971, 1599 RSC; J. W. Cornforth, R. H. Cornforth, G. Popjak and I. Y. Gore, Biochemistry, 1958, 69, 146 CAS; J. W. Cornforth, R. H. Cornforth, C. Donninger and G. Popjak, Proc. R. Soc. London, Ser. B, 1966, 163, 492 Search PubMed; G. Popjak, D. S. Goodman, J. W. Cornforth, R. H. Cornforth and R. Ryhage, Biochem. Biophys. Res. Commun., 1961, 4, 138 CAS; G. Popjak, D. S. Goodman, J. W. Cornforth, R. H. Cornforth and R. Ryhage, J. Biol. Chem., 1961, 236, 1934 CAS; For a review, see C. D. Poulter and H. C. Rilling, in Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter and S. L. Porter, Wiley, New York, 1981, vol. 1, p. 161 Search PubMed.
  2. G. A. Sprenger, U. Schorken, T. Wiegert, S. Grolle, A. A. Graaf, S. V. Taylar, T. P. Begley, S. Bringer-Meyer and H. Sahm, Proc. Natl. Acad. Sci. U.S.A., 1998, 94, 12957; L. M. Lois, N. Campos, S. R. Putra, K. Danielsen, M. Rohmer and A. Boronat, Proc. Natl. Acad. Sci. U.S.A., 1998, 95, 2105 CrossRef CAS For a review, see W. Eisenreich, M. Schwarz, A. Cartayrade, D. Arigoni, M. H. Zenk and A. Bacher, Chem. Biol., 1998, 5, 221 Search PubMed.
  3. J.-L. Giner, B. Jaun and D. Arigoni, Chem. Commun., 1998, 1857 RSC.
  4. F. M. Hahn, J. A. Baker and C. D. Poulter, J. Bacteriol., 1996, 178, 619 CAS The cloning and characterization of the E. coli isomerase has been submitted for publication elsewhere.
  5. L. C. Tarshis, M. Yan, C. D. Poulter and J. C. Sacchettini, Biochemistry, 1994, 33, 10871 CrossRef CAS.
  6. F. M. Hahn and C. D. Poulter, J. Biol. Chem., 1995, 270, 11298 CrossRef CAS.
  7. I. P. Street, D. J. Christensen and C. D. Poulter, J. Am. Chem. Soc., 1990, 112, 8577 CrossRef CAS.
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