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DOI: 10.1039/A809809C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 849-854

Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids

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Concepción González-Bello, John R. Coggins, Alastair R. Hawkins and Chris Abell

Abstract

The synthesis of 4-deoxyquinic acid (1b) from (–)-quinic acid (1a) and 4-deoxyshikimic acid (4b) from shikimic acid (4a) respectively are described. 4-Deoxyshikimic acid (4b) was converted enzymatically into 4-deoxy-3-dehydroshikimic acid (3b) using shikimate dehydrogenase. The C(4) hydroxy group is shown not to contribute significantly to substrate specificity for shikimate dehydrogenase. Attempts to synthesise 4-deoxy-3-dehydroquinic acid (2b) are described.

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