Arogenic acid is an intermediate in the biosynthesis of phenylalanine and tyrosine. At physiological pH it exists as its conjugate base arogenate as the acid form is unstable.
Structure of L-Arogenate
| |
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 | |
PubChem CID
|
|
| |
| |
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).
|
Metabolism
editArogenate 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
edit- ^ "ENZYME - 2.6.1.57 aromatic-amino-acid transaminase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 2.6.1.78 aspartate--prephenate aminotransferase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 2.6.1.79 glutamate--prephenate aminotransferase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 4.2.1.51 prephenate dehydratase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 4.2.1.91 arogenate dehydratase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 1.3.1.43 arogenate dehydrogenase". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 1.3.1.79 arogenate dehydrogenase [NAD(P)(+)]". enzyme.expasy.org. Retrieved 2024-03-05.
- ^ "ENZYME - 1.3.1.78 arogenate dehydrogenase (NADP(+))". enzyme.expasy.org. Retrieved 2024-03-05.