3-Dehydroshikimic acid

Last updated
3-Dehydroshikimic acid
3-Dehydroshikimic acid.svg
Names
Preferred IUPAC name
(4S,5R)-4,5-Dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
Other names
3-Dehydroshikimate
3-DHS
(−)-3-DHS
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.162.474 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
    Key: SLWWJZMPHJJOPH-PHDIDXHHSA-N
  • InChI=1/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
    Key: SLWWJZMPHJJOPH-PHDIDXHHBW
  • C1[C@H]([C@@H](C(=O)C=C1C(=O)O)O)O
Properties
C7H8O5
Molar mass 172.136 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Biosynthesis of shikimic acid from 3-dehydroquinate Shikimate pathway 2.png
Biosynthesis of shikimic acid from 3-dehydroquinate

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]

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3
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In enzymology, a shikimate dehydrogenase (EC 1.1.1.25) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">3-dehydroquinate dehydratase</span> Class of enzymes

The enzyme 3-dehydroquinate dehydratase (EC 4.2.1.10) catalyzes the chemical reaction

<span class="mw-page-title-main">3-dehydroquinate synthase</span> Enzyme

The enzyme 3-dehydroquinate synthase catalyzes the chemical reaction

<span class="mw-page-title-main">Chorismate synthase</span>

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References

  1. Banwell, M. G.; Edwards, A. J.; Essers, M.; Jolliffe, K. A. (2003). "Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer". The Journal of Organic Chemistry. 68 (17): 6839–6841. doi:10.1021/jo034689c. PMID   12919063.
  2. Gallic acid pathway on metacyc.org
  3. Dewick, P. M.; Haslam, E. (1969). "Phenol biosynthesis in higher plants. Gallic acid". The Biochemical Journal. 113 (3): 537–542. doi:10.1042/bj1130537. PMC   1184696 . PMID   5807212.
  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. (2011). "Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia)". Plant Molecular Biology. 75 (6): 555–565. doi:10.1007/s11103-011-9739-3. PMC   3057006 . PMID   21279669.