6-Fluoroshikimic acid

Humphreys JL, Lowes DJ, Wesson KA, Whitehead RC (2006) Arene cw-Dihydrodiols -Useful Precursors for the Preparation of Antimetabolites of the Shikimic Acid Pathway Application to the Synthesis of 6,6-Difluoroshikimic Acid and (6S)-6-Fluoroshikimic Acid. Tetrahedron 62 5099... 

Humphreys, J. L., Lowes, D. J., Wesson, K. A. and Whitehead, R. C. (2006) Arene cis-dihydrodiols - useful precursors for the preparation of antimetabolites of the shikimic acid pathway application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid. Tetrahedron, 62, 5099-5108. 

The synthesis of compound (44) as a potential transition-state analogue inhibitor of isochorismate synthase (IS) has been reported/ Compounds (45) and (46) have been synthesized from the known 6-fluoroshikimic acids (J. Chem. Soc., Chem. Commun., 1989, 1386) by treatment first with shikimate kinase then 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase and shown to be competitive inhibitors of chorismate synthase/ ... 

A synthesis of 2-fluoroshikimic acid 91.2 [Scheme 3.91]169 exposes the robust nature of the methylene acetal Hydrolysis of the methoxymethyl ether and methylene acetal in 91.1 required concentrated hydrochloric add at reflux for 17,5 h to give a 60% yield of the target. 

A one pot enzymatic synthesis of (6/ )- and (65 -fluoroshikimic acid from erythrose 4-phosphate and both isomers of 3-fluorophosphoenolpyruvate in the presence of 3-deoxy-D-ara mo-heptulosonic acid 7-phosphate synthase, followed by treatment with 3-dehydroquinate synthase and dehydroquinase simultaneously, then finally shikimate dehydrogenase has been described. ... 

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