8001. l-Pyroglutamic Acid

Nomenclature

CAS number: 98-79-3
5-Oxo-l-proline; 5-oxo-2-pyrrolidinecarboxylic acid; 2-pyrrolidone-5-carboxylic acid; glutimic acid; glutiminic acid; α-aminoglutaric acid lactam; glutamic acid lactam; pyroGlu.
C5H7NO3; mol wt 129.11.
C 46.51%, H 5.46%, N 10.85%, O 37.18%.

Description and references

Cyclized internal amide of l-glutamic acid found in vegetables, fruits, grasses, and molasses. Easily prepd from l-glutamic acid by autoclaving with an equal wt of water at 135-140°: Dearborn, Stekol, US 2528267; purification: Blish, US 2738353 (1950, 1956, both to International Minerals and Chem.). Review: Orlowski, Meister, in The Enzymes vol. 4, P. D. Boyer, Ed. (Academic Press, New York, 3rd ed., 1971) pp 123-151; C. Moret, M. Briley, Trends Pharmacol. Sci. 9, 278-279 (1988).

Chemical structure

Properties

Orthorhombic bisphenoidal crystals from alcohol + petr ether. mp 162-163°. [α]D20 -11.9° (c = 2); [α]D25 -23.6° (c = 5 at pH 7). Sol in water, alcohol, acetone.

Use

In the resolution of racemic amines.