Title: g-Carboxyglutamic Acid
CAS Registry Number: 53861-57-7
CAS Name: 3-Amino-1,1,3-propanetricarboxylic acid
Synonyms: g-carboxy-L-glutamic acid; L-g-carboxyglutamic acid; Gla
Molecular Formula: C6H9NO6
Molecular Weight: 191.14
Percent Composition: C 37.70%, H 4.75%, N 7.33%, O 50.22%
Literature References: Amino acid found in blood coagulation proteins (prothrombin, Factor VII, Factor IX, Factor X,
q.q.v.), plasma proteins and proteins from calcified tissue. Presence of Gla confers metal binding properties to the protein. Discovery in prothrombin: J. Stenflo,
Proc. Natl. Acad. Sci. USA 71, 2730 (1974); G. L. Nelsestuen
et al., J. Biol. Chem. 249, 6347 (1974). Synthesis: S. Danishefsky
et al., J. Am. Chem. Soc. 101, 4385 (1979); of DL-form: H. R. Morris
et al., Biochem. Biophys. Res. Commun. 62, 856 (1975); W. M?rki, R. Schwyzer,
Helv. Chim. Acta 58, 1471 (1975); B. Weinstein
et al., J. Org. Chem. 41, 3634 (1976). Resolution of D- and L-forms: W. M?rki
et al., Helv. Chim. Acta 60, 798 (1977). Biosynthesis by vitamin K-dependent carboxylation of glutamic acid: C. T. Esmon
et al., J. Biol. Chem. 250, 4744 (1975). Metal binding properties: G. L. Nelsestuen
et al., Biochem. Biophys. Res. Commun. 65, 233 (1975); G. L. Nelsestuen,
J. Biol. Chem. 251, 5648 (1976); R. Robertson
et al., ibid. 253, 5880 (1978); S. P. Bajaj
et al., ibid. 257, 3726 (1982). HPLC determn in proteins, bone, urine: M. Kuwada, K. Katayama,
Anal. Biochem. 117, 259 (1981).
Reviews: J. Stenflo, J. W. Suttie,
Annu. Rev. Biochem. 46, 157-172 (1977); R. E. Olson, J. W. Suttie,
Vitam. Horm. 35, 59-108 (1977); J. W. Suttie,
Crit. Rev. Biochem. 8, 191-223 (1980); J. P. Burnier
et al., Mol. Cell. Biochem. 39, 191-207 (1981).
Properties: Crystals, mp 167-167.5° (dec). [a]D20 +35.3° (c = 1 in 6
N HCl).
Melting point: mp 167-167.5° (dec)
Optical Rotation: [a]D20 +35.3° (c = 1 in 6
N HCl)
Derivative Type: DL-Form
Properties: White powder, mp 90-92°.
Melting point: mp 90-92°
