Procysteine

Procysteine
Names
	Other names 2-oxo-4-thiazolidinecarboxylic acid, OTC
Identifiers
CAS Number	19771-63-2 R enantiomer ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:125673;
ChEMBL	ChEMBL442218;
ChemSpider	65323;
DrugBank	DB12224;
ECHA InfoCard	100.127.075
EC Number	606-375-2;
PubChem CID	72390;
UNII	X7063P804E;
CompTox Dashboard (EPA)	DTXSID501318247 ;
	InChI InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1 Key: BMLMGCPTLHPWPY-REOHCLBHSA-N;
	SMILES C1[C@H](NC(=O)S1)C(=O)O;
Properties
Chemical formula	C4H5NO3S
Molar mass	147.15 g·mol−1
Appearance	white solid
Density	1.709 g/cm3
Melting point	168–170 °C (334–338 °F; 441–443 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ 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.
^ ^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.
^ 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.

[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.

[Analyt-2] 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.

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