Aspartic Acid
Title: Aspartic Acid
CAS Registry Number: 56-84-8
CAS Name: L-Aspartic acid
Additional Names: Asp; D; aminosuccinic acid; asparagic acid; asparaginic acid; (S)-aminobutanedioic acid; 1-amino-1,2-carboxyethane; asparaginsäure (German)
Molecular Formula: C4H7NO4
Molecular Weight: 133.10
Percent Composition: C 36.10%, H 5.30%, N 10.52%, O 48.08%
Literature References: Non-essential amino acid for human development. First identified as the acid hydrolysis product of asparagine, q.v.: A. Plisson, J. Pharm. 13, 477 (1827); later isolated from protein: H. Ritthausen, J. Prakt. Chem. 103, 233, 239 (1868). Early chemistry and biochemistry: Amino Acids and Proteins, D. M. Greenberg, Ed. (Charles C. Thomas, Springfield, IL, 1951) 950 pp., passim; J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids vol 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 1856-1878, passim. Synthesis of optically active forms: K. Harada, K. Matsumoto, J. Org. Chem. 31, 2985 (1966); of labelled form: A. Ivanof et al., Anal. Biochem. 110, 267 (1981). Crystal structure: B. Dawson, Acta Crystallogr. 33B, 882 (1977). Excitatory neurotransmitter: H. McLennan, H. V. Wheal, Can. J. Physiol. Pharmacol. 54, 70 (1976). Role in protein activity: D. W. Urry et al., Biopolymers 34, 889 (1994); J. M. Denu et al., Biochemistry 34, 3396 (1995). Racemization with age in dentin: N. Saleh et al., Calcif. Tissue Int. 53, 103 (1993). Review of metabolism and pathology: L. D. Stegink, J. Toxicol. Environ. Health 2, 215-242 (1976). Review of role as excitatory amino acid: P. J. Roberts, S. W. Davies, Biochem. Soc. Trans. 15, 218-219 (1986); of use in forensics: E. R. Waite et al., Forensic Sci. Int. 103, 113-124 (1999); of pathobiology of age-related racemization in proteins: S. Ritz-Timme, M. J. Collins, Ageing Res. Rev. 1, 43-59 (2002).
Properties: Orthorhombic bisphenoidal leaflets or rods, mp 270-271° (sealed capillary, preheated bath). [a]D20 +25.0° (c = 1.97 in 6N HCl). d12.5 1.661. pK1 1.88; pK2 3.65; pK3 9.60. Soly in water at 20°, 30°: 1 g/222.2 ml, 1 g/149.9 ml. Forms supersatd solns easily. More soluble in salt solns; sol in acids, alkalies. Insol in alcohol.
Melting point: mp 270-271° (sealed capillary, preheated bath)
pKa: pK1 1.88; pK2 3.65; pK3 9.60
Optical Rotation: [a]D20 +25.0° (c = 1.97 in 6N HCl)
Density: d12.5 1.661
 
Derivative Type: D-Form
CAS Registry Number: 1783-96-6
Additional Names: D-Asp
Literature References: Occurs naturally although to a lesser extent than the L-form. Formed by non-enzymatic racemization in ageing protein. Purification and characterization from bovine lens: N. Fujii et al., Biochim. Biophys. Acta 999, 239 (1989); from tissue of the mollusc, Aplysia kurodai: M. Sato et al., Biochem. J. 263, 617 (1989). Review of industrial production by microorganisms: S. Takamatsu, T. Tosa, Bioprocess Technol. 16, 25-35 (1993).
Properties: [a]D25 -2.0° (c = 3.93 in 5N HCl).
Optical Rotation: [a]D25 -2.0° (c = 3.93 in 5N HCl)
 
Derivative Type: Compound with L-arginine
CAS Registry Number: 3054-35-1
Additional Names: Arginine L-aspartate
Trademarks: Sargenor (Viatris)
Molecular Formula: C10H21N5O6
Molecular Weight: 307.30
Percent Composition: C 39.08%, H 6.89%, N 22.79%, O 31.24%
 
Derivative Type: Compound with L-ornithine see Ornithine
 
Derivative Type: N-Acetyl-L-aspartic acid
CAS Registry Number: 997-55-7
Additional Names: NAA
Molecular Formula: C6H9NO5
Molecular Weight: 175.14
Percent Composition: C 41.15%, H 5.18%, N 8.00%, O 45.68%
Literature References: Found in nervous system; second most abundant free amino acid in mammals. Review: D. L. Birken, W. H. Oldendorf, Neurosci. Biobehav. Rev. 13, 23-31 (1989).
 
Use: Nutritional supplement; in forensic determn of age.

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