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Issue 8, 1999
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Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids

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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Article type: Paper
DOI: 10.1039/A809809C
Citation: J. Chem. Soc., Perkin Trans. 1, 1999, 849-854
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    Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids

    C. González-Bello, J. R. Coggins, A. R. Hawkins and C. Abell, J. Chem. Soc., Perkin Trans. 1, 1999, 849
    DOI: 10.1039/A809809C

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