13-01838. β-Carboxyaspartic Acid [Archived]

Nomenclature

CAS number: 75898-26-9
2-Amino-1,1,2-ethanetricarboxylic acid; Asa.
C5H7NO6; mol wt 177.11.
C 33.91%, H 3.98%, N 7.91%, O 54.20%.

Description and references

Amino acid found in ribosomal proteins of E. coli; homolog of γ-carboxyglutamic acid. Isoln and synthesis of dl-form: M. R. Christy et al., J. Am. Chem. Soc. 103, 3935 (1981). Synthesis of dl-form: E. B. Henson et al., Tetrahedron 37, 2561 (1981); N. E. Dixon, A. M. Sargeson, J. Am. Chem. Soc. 104, 6716 (1982). Quantitative analysis method: P. V. Hauschka et al., Anal. Biochem. 108, 57 (1980). Chemical reactivity: M. R. Christy, T. H. Koch, J. Am. Chem. Soc. 104, 1771 (1982). Crystal structure and pKa values of dl-zwitterion: B. Richey et al., Biochemistry 21, 4819 (1982). Asymmetric synthesis of d-form: R. M. Williams et al., J. Am. Chem. Soc. 110, 482 (1988). Review: T. H. Koch et al., Methods Enzymol. 107, 563-575 (1984).

Chemical structure

Derivative

dl-Form hydrochloride.

Nomenclature

CAS number: 81156-58-3
C5H7NO6.HCl; mol wt 213.57.
C 28.12%, H 3.78%, N 6.56%, O 44.95%, Cl 16.60%.

Properties

White crystalline powder. pK1 0.8 ±0.2, pK2 2.5 ±0.1, pK3 4.7 ±0.1, pK4 10.9 ±0.1.

Derivative

d-Form hydrochloride.

Nomenclature

CAS number: 111934-05-5
C5H7NO6.HCl; mol wt 213.57.
C 28.12%, H 3.78%, N 6.56%, O 44.95%, Cl 16.60%.

Properties

White solid, [α]D25 13.25° (c = 0.8 in H2O, pH 2.56).

Status

This monograph has been retired and is no longer subject to revision or update.