Arogenic acid

Arogenic acid

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
CAS Number	53078-86-7 (L) Y
3D model (JSmol)	Interactive image Zwitterion: Interactive image
Beilstein Reference	4458841
ChEBI	CHEBI:17530  Y
ChemSpider	28533971  Y
KEGG	C00826
PubChem CID	25244469
InChI 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
SMILES 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
Chemical formula	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). Infobox references

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

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]}

L-arogenate

+ NAD⁺

 

 

 

CO₂

 

CO₂

 

L-tyrosine

+ NADH

 

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.
9. 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.
10. 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.