Joanna M. Harris, William J. Watkins, Alastair R. Hawkins, John R. Coggins and Chris Abell
J. Chem. Soc., Perkin Trans. 1, 1996, 2371-2377
DOI:
10.1039/P19960002371,
Paper
Syntheses of 5-deoxydehydroquinic acid and 4,5-dideoxydehydroquinic acid from quinic acid are described. These substrate analogues were tested against the mechanistically-distinct type I and type II dehydroquinases. The C-4 hydroxy group of the substrate is shown to be important for imine formation on the type I enzyme but appears not to contribute significantly to specificity on the type II dehydroquinase.