4825. Hydroxyglutamic Acid

Nomenclature

CAS number: 533-62-0
β-Hydroxyglutamic acid; α-amino-β-hydroxyglutaric acid.
C5H9NO5; mol wt 163.13.
C 36.81%, H 5.56%, N 8.59%, O 49.04%.

Description and 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 α-isonitrosoacetone dicarboxylate: Harington, Randall, Biochem. J. 25, 1917 (1931); Levene, Schormüller, J. Biol. Chem. 106, 595 (1934).

Chemical structure

Derivative

l-Form.

Properties

Prisms from water. Dec 135° (if completely anhydrous; hydrated crystals soften at 100-105°). [α]D20 +1.2° (c = 2); [α]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.

Derivative

dl-Form.

Properties

Orthorhombic prisms, needles from water. Dec 198°. Very sol in hot water.