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Arogenic acid
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 Structure of L-Arogenate
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| Names | |
|---|---|
| IUPAC name
1-[(2S)-2-amino-2-carboxyethyl]-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
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| Other names
(1s,4s)-1-(2-Amino-2-carboxyethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
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| Identifiers | |
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3D model (JSmol)
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| 4458841 | |
| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| 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).
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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.
Metabolism
[edit]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:[9][10]
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.
- ^ Stenmark SL, Pierson DL, Jensen RA, Glover GI (1974). "Blue-green bacteria synthesise L-tyrosine by the pretyrosine pathway". Nature. 247 (439): 290–2. Bibcode:1974Natur.247..290S. doi:10.1038/247290a0. PMID 4206476. S2CID 4200115.
- ^ Byng G, Whitaker R, Flick C, Jensen RA (1981). "Enzymology of L-tyrosine biosynthesis in corn (Zea mays)". Phytochemistry. 20 (6): 1289–1292. Bibcode:1981PChem..20.1289B. doi:10.1016/0031-9422(81)80023-4.