3-Dehydroshikimic acid explained

3-Dehydroshikimic acid is a chemical compound related to shikimic acid. 3-DHS is available in large quantity through engineering of the shikimic acid pathway.^[1]

Metabolism

Biosynthesis: The enzyme 3-dehydroquinate dehydratase uses 3-dehydroquinate to produce 3-dehydroshikimate and H₂O.

3-Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor.

Gallic acid is also formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound spontaneously rearranges to gallic acid.^{[2] [3] [4]}

Notes and References

1. Banwell . M. G. . Edwards . A. J. . Essers . M. . Jolliffe . K. A. . Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer . 10.1021/jo034689c . The Journal of Organic Chemistry . 68 . 17 . 6839–6841 . 2003 . 12919063.
2. http://www.metacyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-6707 Gallic acid pathway on metacyc.org
3. Dewick . P. M. . Haslam . E. . Phenol biosynthesis in higher plants. Gallic acid . The Biochemical Journal . 113 . 3 . 537–542 . 1969 . 5807212 . 1184696 . 10.1042/bj1130537.
4. Muir . R. M. . Ibáñez . A. M. . Uratsu . S. L. . Ingham . E. S. . Leslie . C. A. . McGranahan . G. H. . Batra . N. . Goyal . S. . Joseph . J. . Jemmis . E. D. . Dandekar . A. M. . 10.1007/s11103-011-9739-3 . Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia) . Plant Molecular Biology . 75 . 6 . 555–565 . 2011 . 21279669. 3057006 .