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Browsing Chemistry publications by Author "Abell, C."
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Item Metadata only A Convenient Method for the Synthesis of Dehydroquinic Acid(Marcel Dekker Inc, 2003) Le Sann, C.; Abell, C.; Abell, A.A convenient synthesis of dehydroquinic acid and its corresponding methyl ester are described. Protection of the trans diol of quinic acid, followed by PCC oxidation, gave fully protected dehydroquinic acid. This gave methyl dehydroquinate on mild acid catalyzed hydrolysis. Ester hydrolysis then gave potassium dehydroquinate which was treated with amberlite to afford dehydroquinic acid.Item Metadata only A simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase(Royal Society of Chemistry, 2002) Le Sann, C.; Abell, C.; Abell, A.A number of routes to 3-hydroxyiminodehydroquinate 4, one of the most potent inhibitors of type II dehydroquinase that is currently known, have been investigated. Methods based on the existing literature synthesis, i.e. oxime formation of a suitably C-4 and C-5 protected methyl 3-dehydroquinate derivative were initially studied. Benzoyl protection as in 11 did give the desired product but in low overall yield. An alternative BBA protection strategy starting with 7 was successful in generating a C-4/C-5 analogue of the desired oxime 4 in high yield. Further investigation revealed that it was unnecessary to protect the dehydroquinate precursor, hence the potassium salt corresponding to oxime 4 was simply synthesised as a single isomer from methyl dehydroquinate 10.Item Metadata only Design and synthesis of aromatic inhibitors of anthranilate synthase(Royal Soc Chemistry, 2005) Payne, R.; Bulloch, E.; Abell, A.; Abell, C.Anthranilate synthase catalyses the conversion of chorismate to anthranilate, a key step in tryptophan biosynthesis. A series of 3-(1-carboxy-ethoxy) benzoic acids were synthesised as chorismate analogues, with varying functionality at C-4, the position of the departing hydroxyl group in chorismate. Most of the compounds were moderate inhibitors of anthranilate synthase, with inhibition constants between 20–30 μM. The exception was 3-(1-carboxy-ethoxy) benzoic acid, (C-4 = H), for which K₁ = 2.4 μM. These results suggest that a hydrogen bonding interaction with the active site general acid (Glu309) is less important than previously assumed for inhibition of the enzyme by these aromatic chorismate analogues.Item Metadata only Inhibition studies on salicylate synthase(Royal Soc Chemistry, 2005) Payne, R.; Kerbarh, O.; Miguel, R.; Abell, A.; Abell, C.Analogues of chorismate and isochorismate were designed and tested as potential inhibitors in the first inhibition study against a salicylate synthase.