Arogenic acid is an intermediate in the

biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...

and

tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is ...

. At physiological pH it exists as its conjugate base arogenate as the acid form is unstable.

Metabolism

Arogenate is synthesized from

prephenate Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway. Oc ...

transamination Transamination is a chemical reaction that transfers an amino group to a ketoacid to form new amino acids.This pathway is responsible for the deamination of most amino acids. This is one of the major degradation pathways which convert essential a ...

. This reaction can be catalyzed by several enzymes, including aromatic-amino-acid transaminase,

aspartate—prephenate aminotransferase In enzymology, an aspartate-prephenate aminotransferase () is an enzyme that catalyzes the chemical reaction :L-arogenate + oxaloacetate \rightleftharpoons prephenate + L-aspartate Thus, the two substrates of this enzyme are L-arogenate and oxa ...

and glutamate—prephenate aminotransferase: : prephenate + amino acid → arogenate + keto acid The amino acid in this case can be either

aspartate Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. The L-isomer of aspartic acid is one of the 22 proteinogenic amino acids, i.e., the building blocks of protein ...

glutamate Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a Essential amino acid, non-essential nutrient for humans, meaning that ...

, which turn into

oxaloacetate Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes ...

and 2-oxoglutarate, respectively. Arogenate is then turned into either phenylalanine or tyrosine. When

prephenate dehydratase The enzyme prephenate dehydratase () catalyzes the chemical reaction :prephenate \rightleftharpoons phenylpyruvate + H2O + CO2 This enzyme belongs to the family of lyases, specifically the hydro-lyases, which cleave carbon-oxygen bonds. The syst ...

arogenate dehydratase Arogenate dehydratase (ADT) () is an enzyme that catalyzes the chemical reaction : L-arogenate → L phenylalanine + H2O + CO2 Certain forms of the protein have the potential to catalyze a second reaction, :L-prephenate → L-phenylpyruvate + H2O ...

act upon arogenate, phenylalanine is produced: : arogenate → phenylalanine + H₂O + CO₂ When

arogenate dehydrogenase In enzymology, an arogenate dehydrogenase () is an enzyme that catalyzes the chemical reaction :L-arogenate + NAD+ \rightleftharpoons L-tyrosine + NADH + CO2 Thus, the two substrates of this enzyme are L-arogenate and NAD+, whereas its 3 prod ...

arogenate dehydrogenase (NAD(P)+) In enzymology, an arogenate dehydrogenase AD(P)+'' () is an enzyme that catalyzes the chemical reaction :L-arogenate + NAD(P)+ \rightleftharpoons L-tyrosine + NAD(P)H + CO2 The 3 substrates of this enzyme are L-arogenate, NAD+, and NADP+, w ...

arogenate dehydrogenase (NADP+) In enzymology, an arogenate dehydrogenase (NADP+) () is an enzyme that catalyzes the chemical reaction :L-arogenate + NADP+ \rightleftharpoons L-tyrosine + NADPH + CO2 Thus, the two substrates of this enzyme are L-arogenate and NADP+, wherea ...

acts upon arogenate, tyrosine is produced: : arogenate + NAD(P)⁺ → tyrosine + NAD(P)H + H⁺ + CO₂

References

{{Reflist Aromatic amino acids Dicarboxylic acids