Ornithine
Title: Ornithine
CAS Registry Number: 70-26-8
CAS Name: L-Ornithine
Additional Names: a,d-diaminovaleric acid; 2,5-diaminopentanoic acid
Molecular Formula: C5H12N2O2
Molecular Weight: 132.16
Percent Composition: C 45.44%, H 9.15%, N 21.20%, O 24.21%
Literature References: Non-essential amino acid for human development but is required intermediate in arginine biosynthesis. Found in virtually all vertebrate tissues as well as incorporated into proteins, such as tyrocidine, q.v. Isolation from chicken excreta: M. Jaffe, Ber. 10, 1925 (1877). Early chemistry and biochemistry: J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids (John Wiley and Sons, Inc., New York, 1961) pp. 2477-2491, passim. Review of synthesis: R. Yoshida, Synth. Prod. Util. Amino Acids, T. Kaneko et al., Eds (Kodansha Ltd, Tokyo, Japan, 1974) pp 166-170; of biosynthesis in plants: P. D. Shargool et al., Phytochemistry 27, 1571-1574 (1988). Brief historical review: H. A. Akers, E. V. Dromgoole, Trends Biochem. Sci. 7, 156-157 (1982). Review of metabolism: V. E. Shih, Enzyme 26, 254-258 (1981); of role in CNS functions: N. Seiler, G. Daune-Anglard, Metab. Brain Dis. 8, 151-179 (1993).
Properties: Colorless crystals. [a]D25 +11.5° (c = 6.5). Aq solns are alkaline. pK1¢ 1.94; pK2¢ 8.65; pK3¢ 10.76. Freely sol in water, alc; sparingly sol in ether.
pKa: pK1¢ 1.94; pK2¢ 8.65; pK3¢ 10.76
Optical Rotation: [a]D25 +11.5° (c = 6.5)
 
Derivative Type: L-Form aspartate
CAS Registry Number: 3230-94-2
Additional Names: L-Ornithine-L-aspartate
Trademarks: Hepa-Merz (Merz)
Properties: Crystal structure: D. M. Salunke, M. Vijayan, Int. J. Pept. Protein Res. 22, 154 (1983). Clinical trial in hyperammonemia: J. Fehér et al., Med. Sci. Monit. 3, 669 (1997); S. Stauch et al., J. Hepatol. 28, 856 (1998).
 
Derivative Type: DL-Form
CAS Registry Number: 616-07-9
Properties: Crystals from water. Sparingly sol in alcohol.
 
Therap-Cat: In treatment of hyperammonemia.

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