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Procysteine is an organic compound with the formula CH2NHC(O)SCHCO2H. It is a colorless solid. The compound is classified as a derivative of the heterocycle 2-oxo-1,3-thiazoline. Such rings are prepared by the action of phosgene (or related dehydration reagents[2] on 2-aminoethanethiols, in this case cysteine:

HSCH2CH(NH2)CO2H + COCl2 → CH2NHC(O)SCHCO2H + 2 HCl

The compound hydrolyzes to cysteine.[3] The hydrolysis is catalyzed by 5-oxoprolinase.[2]

References

  1. ^ Dobson, A. J.; Gerkin, R. E. (1998). “(4 R )-(−)-2-Thioxothiazolidine-4-carboxylic Acid (Raphanusamic Acid)”. Acta Crystallographica Section C Crystal Structure Communications. 54 (11): 1634–1637. Bibcode:1998AcCrC..54.1634D. doi:10.1107/S0108270198006416. PMID 9857474.
  2. ^ a b Boettcher, Brian; Meister, Alton (1984). “Synthesis of l -2-oxothiazolidine-4-carboxylic acid”. Analytical Biochemistry. 138 (2): 449–450. doi:10.1016/0003-2697(84)90837-6. PMID 6742422.
  3. ^ Anderson, Mary E. (1998). “Glutathione: An overview of biosynthesis and modulation”. Chemico-Biological Interactions. 111–112: 1–14. Bibcode:1998CBI…111….1A. doi:10.1016/S0009-2797(97)00146-4. PMID 9679538.