Hydroxyglutamic Acid

Title: Hydroxyglutamic Acid
CAS Registry Number: 533-62-0
Additional Names: b-Hydroxyglutamic acid; a-amino-b-hydroxyglutaric acid
Molecular Formula: C5H9NO5
Molecular Weight: 163.13
Percent Composition: C 36.81%, H 5.56%, N 8.59%, O 49.04%
Literature References: An amino acid classified as nonessential with respect to its growth effect in rats. Not among the naturally occurring hydrolytic products of proteins, see Schmidt, Chemistry of the Amino Acids and Proteins (Springfield, Ill., 2nd ed., 1944) p 1090. Synthesis from ethyl a-isonitrosoacetone dicarboxylate: Harington, Randall, Biochem. J. 25, 1917 (1931); Levene, Schormüller, J. Biol. Chem. 106, 595 (1934).
Derivative Type: L-Form
Properties: Prisms from water. Dec 135° (if completely anhydrous; hydrated crystals soften at 100-105°). [a]D20 +1.2° (c = 2); [a]D20 +17.6° (c = 2 in 6N HCl). pK1¢ 2.09; pK2¢ 4.18; pK3¢ 9.20. Freely sol in water, acetic acid. Insol in alc, ether.
pKa: pK1¢ 2.09; pK2¢ 4.18; pK3¢ 9.20
Optical Rotation: [a]D20 +1.2° (c = 2); [a]D20 +17.6° (c = 2 in 6N HCl)
Derivative Type: DL-Form
Properties: Orthorhombic prisms, needles from water. Dec 198°. Very sol in hot water.
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