Title: Arogenic Acid
CAS Registry Number: 53078-86-7
CAS Name: [1(S)-cis]-a-Amino-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-propanoic acid
Additional Names: L-(8S)-b-(1-carboxy-4-hydroxy-2,5-cyclohexadien-1-yl)alanine; arogenate; pretyrosine
Molecular Formula: C10H13NO5
Molecular Weight: 227.21
Percent Composition: C 52.86%, H 5.77%, N 6.16%, O 35.21%
Literature References: Precursor in the biosynthesis of L-phenylalanine and L-tyrosine, distributed widely in nature. Pseudomonad bacteria and plants use both the prephenate and arogenate pathways for L-tyrosine biosynthesis. In cyanobacteria, coryniform bacteria and at least one yeast organism the arogenate pathway has been identified as the sole route of L-tyrosine biosynthesis. Identification of arogenate (pretyrosine) in blue-green algae biosynthesis of L-tyrosine: S. L. Stenmark et al., Nature 247, 290 (1974). Dual enzymic routes to L-tyrosine and L-phenylalanine via arogenate (pretyrosine) in P. aeruginosa: N. Patel et al., J. Biol. Chem. 252, 5839 (1977). Isoln and prepn: R. A. Jensen et al., J. Bacteriol. 132, 896 (1977). Confirmation that arogenate is an obligatory intermediate of L-tyrosine biosynthesis: A. M. Fazel et al., Proc. Natl. Acad. Sci. USA 77, 1270 (1980). Structure and config: L. O. Zamir et al., J. Am. Chem. Soc. 102, 4499 (1980). Synthesis via immobilized microbial proteins: eidem, Bioorg. Chem. 11, 32 (1982). Arogenate pathway of tyrosine and phenylalanine biosynthesis in P. aureofaciens: B. Keller et al., J. Gen. Microbiol. 128, 1199 (1982).
Properties: Unstable. Quantitatively converted to phenylalanine at acidic pH. Forms a disodium salt that is stable in the lyophilized state at basic pH (7.5) and room temperature, but is thermally unstable.