The shikimate pathway. V. Fluorine-containing analogues of 3-deoxy-D-arabino hept-2-ulosonate-7-phosphate (DAHP).
(3R) and (3S) 3-deoxy-3-fluoro-7-phospho-D-arabino hept-2-ulosonic acids (3R and 3S-3F-DAHP) the 3-fluoro analogues of DAHP were synthesized from the corresponding 2-deoxy-2-fluoro hexose-6-phosphates. 3R- and 3S-3F-DAHP were tested as substrates for 3-dehydroquinate synthetase from E. coli. Determination of kinetic parameters showed that their apparent Km and Vm were in the same order of magnitude for these two compounds. Further conversion of 3R- and 3S-3F-DAHP into (6R) and (6S) 6-fluoro dehydroshikimate and (6R) and (6S) 6-fluoro shikimate, respectively, was investigated and results are discussed.
D055598:Chemical Phenomena; D002621:Chemistry; D004926:Escherichia coli / Q000201:enzymology; D005461:Fluorine; D007700:Kinetics; D008190:Lyases / Q000378:metabolism; D019761:Phosphorus-Oxygen Lyases; D012765:Shikimic Acid / Q000378:metabolism*; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000378:metabolism
D013403:Sugar Phosphates; C013469:3-deoxy-D-arabino-heptulosonate-7-phosphate; D005461:Fluorine; D012765:Shikimic Acid; D008190:Lyases; C020001:3-dehydroquinate synthetase; D019761:Phosphorus-Oxygen Lyases