L-2-Oxo-4-thiazolidinecarboxylic acid
Title: L-2-Oxo-4-thiazolidinecarboxylic acid
CAS Registry Number: 19771-63-2
CAS Name: (4R)-2-Oxo-4-thiazolidinecarboxylic acid
Additional Names: OTCA; OTC
Trademarks: Procysteine (Baxter)
Molecular Formula: C4H5NO3S
Molecular Weight: 147.15
Percent Composition: C 32.65%, H 3.42%, N 9.52%, O 32.62%, S 21.79%
Literature References: Cysteine prodrug. Prepn: J. A. Maclaren, Aust. J. Chem. 21, 1891 (1968); T. Kömives, Org. Prep. Proced. Int. 21, 251 (1989). Crystal structure: N. Ramasubbu, R. Parthasarathy, Int. J. Pept. Protein Res. 34, 153 (1989). Precursor for cysteine and use as glutathione biosynthesis stimulant: J. M. Williamson et al., Proc. Natl. Acad. Sci. USA 79, 6246 (1982); in chicks: T. K. Chung et al., J. Nutr. 120, 158 (1990). Toxicity: R. D. White et al., Acute Toxic. Data 1, 164 (1992); R. D. White et al., Toxicol. Lett. 69, 15 (1993). Clinical evaluation in HIV infection: G. Giorgi et al., Curr. Ther. Res. 52, 461 (1992); in asymptomatic HIV infection: R. C. Kalayjian et al., J. Acquired Immune Defic. Syndr. 7, 369 (1994). HPLC determn in plasma: L. W. Webb et al., J. Chromatogr. B 654, 257 (1994).
Properties: Colorless cubes, mp 171-173° (dec) (Maclaren). Also reported as white crystals, mp 173-174° (Kömives). pKa (22°): 3.32. [a]D20 -59.4° (c = 2). Readily sol in alcohol. Insol in benzene and ethyl acetate.
Melting point: mp 171-173° (dec) (Maclaren); mp 173-174° (Kömives)
pKa: pKa (22°): 3.32
Optical Rotation: [a]D20 -59.4° (c = 2)

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