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3-Dehydroshikimic acid

3-DHS (−)-3-DHS

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.

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.

:[[Image:Shikimate pathway 2.png|left|500px|thumb|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.{{Cite journal

References

(2003). "Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer". The Journal of Organic Chemistry.
[http://www.metacyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-6707 Gallic acid pathway on metacyc.org]
(2011). "Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia)". Plant Molecular Biology.

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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