Oudenone

Last updated
Oudenone
Oudenone.png
Oudenone molecule ball.png
Names
Preferred IUPAC name
2-[(5S)-5-Propyloxolan-2-ylidene]cyclopentane-1,3-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H16O3/c1-2-3-8-4-7-11(15-8)12-9(13)5-6-10(12)14/h8H,2-7H2,1H3/t8-/m0/s1 Yes check.svgY
    Key: AFHDYMGMZUYZQT-QMMMGPOBSA-N Yes check.svgY
  • InChI=1/C12H16O3/c1-2-3-8-4-7-11(15-8)12-9(13)5-6-10(12)14/h8H,2-7H2,1H3/t8-/m0/s1
    Key: AFHDYMGMZUYZQT-QMMMGPOBBE
  • O=C1C(/C(=O)CC1)=C2/O[C@H](CC2)CCC
Properties
C12H16O3
Molar mass 208.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oudenone is a molecule found in fungus metabolism. [1] It is an inhibitor of the enzyme tyrosine hydroxylase.

Related Research Articles

Tyrosine hydroxylase Enzime found in Homo sapiens that converts l-tyrosine to l-dopa, the precursor of cathecolamines

Tyrosine hydroxylase or tyrosine 3-monooxygenase is the enzyme responsible for catalyzing the conversion of the amino acid L-tyrosine to L-3,4-dihydroxyphenylalanine (L-DOPA). It does so using molecular oxygen (O2), as well as iron (Fe2+) and tetrahydrobiopterin as cofactors. L-DOPA is a precursor for dopamine, which, in turn, is a precursor for the important neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline). Tyrosine hydroxylase catalyzes the rate limiting step in this synthesis of catecholamines. In humans, tyrosine hydroxylase is encoded by the TH gene, and the enzyme is present in the central nervous system (CNS), peripheral sympathetic neurons and the adrenal medulla. Tyrosine hydroxylase, phenylalanine hydroxylase and tryptophan hydroxylase together make up the family of aromatic amino acid hydroxylases (AAAHs).

References

  1. ↑ Tsantrizos YS, Yang X, McClory A (September 1999). "Studies on the Biosynthesis of the Fungal Metabolite Oudenone. 2. Synthesis and Enzymatic Cyclization of an alpha-Diketone, Open-Chain Precursor into Oudenone in Cultures of Oudemansiella radicata". J. Org. Chem. 64 (18): 6609–6614. doi:10.1021/jo9901135. PMID   11674663.


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