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

Lookup NU author(s): Professor Alastair Hawkins


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The synthesis of 4-deoxyquinic acid (Ib) from (-)-quinic acid (la) 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.

Publication metadata

Author(s): Gonzalez-Bello C, Coggins TJR, Hawkins AR, Abell C

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society - Perkin Transactions 1

Year: 1999

Issue: 8

Pages: 849-854

Print publication date: 01/01/1999

ISSN (print): 0300-922X

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry


DOI: 10.1039/A809809C


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