3-Dehydroshikimic acid

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
3-Dehydroshikimic acid
Chemical structure of 3-dehydroshikimic acid.
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 Edit this at Wikidata
  • 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).
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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

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]

References

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