Arogenic acid

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Arogenic acid

Arogenic acid without specified stereochemistry
Names
IUPAC name
1-[(2S)-2-amino-2-carboxyethyl]-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Other names
(1s,4s)-1-(2-Amino-2-carboxyethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Identifiers
3D model (JSmol)
4458841
ChEBI
ChemSpider
KEGG
  • InChI=1S/C10H13NO5/c11-7(8(13)14)5-10(9(15)16)3-1-6(12)2-4-10/h1-4,6-7,12H,5,11H2,(H,13,14)(H,15,16)/p-1/t6?,7-,10?/m0/s1
    Key: MIEILDYWGANZNH-DSQUFTABSA-M
  • C1=CC(C=CC1O)(CC(C(=O)[O-])N)C(=O)O
  • Zwitterion: C1=CC(C=CC1O)(CC(C(=O)[O-])[NH3+])C(=O)[O-]
Properties
C10H13NO5
Molar mass 227.216 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Arogenic acid is an intermediate in the biosynthesis of phenylalanine and tyrosine. Its conjugate base is arogenate.

Metabolism

Arogenate is synthesized from prephenate by transamination. This reaction can be catalyzed by several enzymes, including aromatic-amino-acid transaminase,[1] aspartate—prephenate aminotransferase[2] and glutamate—prephenate aminotransferase:[3]

prephenate + amino acid → arogenate + keto acid

The amino acid in this case can be either aspartate or glutamate, which turn into oxaloacetate and 2-oxoglutarate, respectively.

Arogenate is then turned into either phenylalanine or tyrosine. When prephenate dehydratase[4] or arogenate dehydratase[5] act upon arogenate, phenylalanine is produced:

arogenate → phenylalanine + H2O + CO2

When arogenate dehydrogenase,[6] arogenate dehydrogenase (NAD(P)+)[7] or arogenate dehydrogenase (NADP+)[8] acts upon arogenate, tyrosine is produced:

arogenate + NAD(P)+ → tyrosine + NAD(P)H + H+ + CO2

References

  1. ^ "ENZYME - 2.6.1.57 aromatic-amino-acid transaminase". enzyme.expasy.org. Retrieved 2024-03-05.
  2. ^ "ENZYME - 2.6.1.78 aspartate--prephenate aminotransferase". enzyme.expasy.org. Retrieved 2024-03-05.
  3. ^ "ENZYME - 2.6.1.79 glutamate--prephenate aminotransferase". enzyme.expasy.org. Retrieved 2024-03-05.
  4. ^ "ENZYME - 4.2.1.51 prephenate dehydratase". enzyme.expasy.org. Retrieved 2024-03-05.
  5. ^ "ENZYME - 4.2.1.91 arogenate dehydratase". enzyme.expasy.org. Retrieved 2024-03-05.
  6. ^ "ENZYME - 1.3.1.43 arogenate dehydrogenase". enzyme.expasy.org. Retrieved 2024-03-05.
  7. ^ "ENZYME - 1.3.1.79 arogenate dehydrogenase [NAD(P)(+)]". enzyme.expasy.org. Retrieved 2024-03-05.
  8. ^ "ENZYME - 1.3.1.78 arogenate dehydrogenase (NADP(+))". enzyme.expasy.org. Retrieved 2024-03-05.
Retrieved from "https://mdwiki.org/wiki/Arogenic_acid"