5177. l-Isoglutamine

Nomenclature

CAS number: 636-65-7
(4S)-4,5-Diamino-5-oxopentanoic acid; 4-amino-l-glutaramic acid; glutamic acid α-amide.
C5H10N2O3; mol wt 146.14.
C 41.09%, H 6.90%, N 19.17%, O 32.84%.

Description and references

Prepn by the action of NH3 on N-carbobenzyloxy-l-glutamic acid anhydride: Kozo Narita, J. Chem. Soc. Jpn. Pure Chem. Sect. 74, 832 (1953); from 1-tosylpyroglutamide by reduction with Na in NH3: Swan, du Vigneaud, J. Am. Chem. Soc. 76, 3110 (1954); from the γ-methyl ester of N-tritylglutamic acid: Amiard, Heymes, US 2927118 (1960 to UCLAF).

Chemical structure

Properties

Crystals from acetone, dec 181°. [α]D21 +20.5° (c = 6.1 in H2O). pK1′ 3.81; pK2′ 7.88. Sol in water. Sparingly sol in organic solvents.