Chemistry:Procysteine

From HandWiki

Procysteine is an organic compound with the formula CH
2
NHC(O)SCHCO
2
H
. 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[1] on 2-aminoethanethiols, in this case cysteine:

HSCH
2
CH(NH
2
)CO
2
H + COCl
2
→ CH
2
NHC(O)SCHCO
2
H + 2 HCl

The compound hydrolyzes to cysteine.[2] The hydrolysis is catalyzed by 5-oxoprolinase.[1]

References

  1. 1.0 1.1 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. 
  2. Anderson, Mary E. (1998). "Glutathione: An overview of biosynthesis and modulation". Chemico-Biological Interactions 111-112: 1–14. doi:10.1016/S0009-2797(97)00146-4. PMID 9679538. Bibcode1998CBI...111....1A.