References of (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
Title: Cystine
CAS Registry Number: 56-89-3
CAS Name: L-Cystine
Synonyms: [
R-(
R*,R*)]-3,3¢-dithiobis[2-aminopropanoic acid]; dicysteine; b,b¢-dithiodialanine; a-diamino-b-dithiolactic acid; b,b¢-diamino-b,b¢-dicarboxydiethyl disulfide; bis(b-amino-b-carboxyethyl) disulfide
Trademarks: Gelucystine (Parke-Davis)
Molecular Formula: C6H12N2O4S2
Molecular Weight: 240.30
Percent Composition: C 29.99%, H 5.03%, N 11.66%, O 26.63%, S 26.69%
Literature References: Non-essential amino acid for human development. Formed by the dimerization of two cysteines,
q.v. through the sulfur. These disulfide bridges occur both within and between polypeptides; often found in extracellular proteins. First amino acid described in 1810 by Wollaston. Isoln from horn hydrolysate: K. A. H. M?rner,
Z. Physiol. Chem. 28, 595 (1899). 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 vols 1-3 (John Wiley and Sons, Inc., New York, 1961) pp. 1879-1928,
passim. Distribution in protein: R. C. Fahey
et al., J. Mol. Evol. 10, 155 (1977). Review of lysosomal transport including pathophysiology: W. Gahl in
Pathophysiol. Lysosomal Transp., J. G. Thoene, Ed. (CRC Press, Boca Raton, FL, 1992) pp 45-71. Review of thermodynamics and kinetics: T. R. Ralph
et al., J. Electroanal. Chem. 375, 1-15 (1994); of electrosynthesis:
eidem, ibid. 17-27.
Properties: Hexagonal tablets from water, dec 260-261° (sealed tube). [a]D20 -223.4° (1.0
N HCl). pK1 1; pK2 2.1; pK3 8.02; pK4 8.71 at 35°. Soly in water (g/l) at 25°: 0.112; at 50°: 0.239; at 75°: 0.523; at 100°: 1.142. Quite sol in aq solns below pH 2 or above pH 8. Soly curves: Sano,
Biochem. Z. 168, 14 (1926). Insol in alc. Absorption spectrum: Marchlewski, Nowotonowna,
Bull. Soc. Chim. Fr. [4]
39, 163, 166 (1926).
pKa: pK1 1; pK2 2.1; pK3 8.02; pK4 8.71 at 35°
Optical Rotation: [a]D20 -223.4° (1.0
N HCl)
Derivative Type: D-Form
CAS Registry Number: 349-46-2
Properties: Crystals. [a]D20 +223° (1.0
N HCl). Soly in water at 25°: 0.057 g/l.
Optical Rotation: [a]D20 +223° (1.0
N HCl)
Derivative Type: DL-Form
CAS Registry Number: 923-32-0
Properties: Crystals. Soly in water at 25°: 0.057 g/l.
Derivative Type: meso-Form
CAS Registry Number: 6020-39-9
Properties: Crystals. Soly in water: 0.056 g/l.