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Enzymatic synthesis of (6R)- and (6S)-fluoroshikimic acids

✍ Scribed by Peter J. Duggan; Emily Parker; John Coggins; Chris Abell

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 321 KB
Volume: 5
Category: Article
ISSN: 0960-894X
DOI: 10.1016/0960-894x(95)00405-i

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✦ Synopsis

6-Fluoroshikimates have interesting antibiotic properties. The enzymatic preparation of (6R)-and (6S)-fluoroshikimates from 3-fluorophosphoenolpyruvate is described. The multistep enzymatic conversion is followed by UV and 19F NMR spectroscopy.

The shikimic acid pathway is an established target for herbicidal action. 1 Recently there has been interest

in the pathway as a potential site of antimicrobial action following reports of the antibiotic properties of 6fluoroshikimic acids. 2 It was reasoned that (6R)-6-fluoroshikimate might be converted in vivo into the corresponding (6R)-6-fluoro-5-enolpyruvylshikimate 3-phosphate [(6R)-fluoroEPSP, 8b], which could inhibit the elimination reaction catalysed by chorismate synthase (Scheme 1). This hypothesis gained support when it was shown that (6R)-and (6S)-6-fluoroEPSPs (8b and 8e) are competitive inhibitors of Neurospora crassa chorismate synthase. 3 Moreover, it has been shown that when 8b is incubated with Escherichia coli chorismate synthase a stable flavin semiquinone radical is formed and the normal catalytic cycle is halted. 4 However these

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