- Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid
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(2R)-2-Bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid ? have each been synthesised in six steps from quinic acid via the common intermediate 6. The syntheses exploit the selective protection of the 4-hydroxy group of the quinic acid lactone 3 with tert-butyldimethylsilyl chloride. ? IUPAC names: (1S,2R,4S,5R)-2-bromo-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid and (1S,2R,4S,5R)-2-fluoro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid, respectively.
- Manthey, Michael K.,Gonzalez-Bello, Concepcion,Abell, Chris
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p. 625 - 628
(2007/10/03)
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- Comparison of the substrate specificity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid
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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.
- Harris, Joanna M.,Watkins, William J.,Hawkins, Alastair R.,Coggins, John R.,Abell, Chris
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p. 2371 - 2377
(2007/10/03)
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