Cysteine sulfinic acid

Cysteine sulfinic acid
Names
	IUPAC name 2-amino-3-sulfinopropanoic acid
Identifiers
CAS Number	2381-08-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16345 ;
ChemSpider	1266065 ;
ECHA InfoCard	100.012.935
IUPHAR/BPS	5447;
MeSH	cysteine+sulfinic+acid
PubChem CID	1549098;
UNII	UZY4HYK4ZX ;
CompTox Dashboard (EPA)	DTXSID20862546 ;
	InChI InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 Key: ADVPTQAUNPRNPO-REOHCLBHSA-N ; InChI=1/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 Key: ADVPTQAUNPRNPO-REOHCLBHBM;
	SMILES O=C(O)[C@@H](N)CS(=O)O;
Properties
Chemical formula	C3H7NO4S
Molar mass	153.15698
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Cysteine sulfinic acid, also known as 3-sulfino-L-alanine, [1] is an amino acid containing a sulfinic acid functional group. It is a white solid that is soluble in water. It is an intermediate in cysteine metabolism. It is not a coded amino acid, but is produced post-translationally.

Cysteine sulfinic acid is derived from cysteine. Cysteine is formed from cystathionine via the cystathionine gamma-lyase enzyme, and is either broken down by cysteine lyase or cystathionine gamma-lyase or enters the cysteine sulfinic acid pathway where it is oxidized by cysteine dioxygenase to form cysteine sulfinic acid. Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine, which in turn is oxidized by hypotaurine dehydrogenase to yield taurine.[2] Proteins containing this residue are found at the active site of some nitrile hydratases.[3]

Cysteine sulfinic acid (2) is an intermediate in the conversion of cysteine (1) to taurine (4).

References

https://pubchem.ncbi.nlm.nih.gov/compound/L-Cysteinesulfinic_acid
Sumizu K (1962). "Oxidation of hypotaurine in rat liver". Biochim. Biophys. Acta. 63: 210–212. doi:10.1016/0006-3002(62)90357-8. PMID 13979247.
Isao Endo, Masaki Nojiri, b, Masanari Tsujimura, Masayoshi Nakasako, Shigehiro Nagashima, Masafumi Yohda, Masafumi Odaka "Focused Review: Fe-type nitrile hydratase"Journal of Inorganic Biochemistry 2001, Volume 83, Issue 4, February 2001, Pages 247–253. doi:10.1016/S0162-0134(00)00171-9

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[1] ttps://pubchem.ncbi.nlm.nih.gov/compound/L-Cysteinesulfinic_acid

[2] Sumizu K (1962). "Oxidation of hypotaurine in rat liver". Biochim. Biophys. Acta. 63: 210–212. doi:10.1016/0006-3002(62)90357-8. PMID 13979247.

[3] Isao Endo, Masaki Nojiri, b, Masanari Tsujimura, Masayoshi Nakasako, Shigehiro Nagashima, Masafumi Yohda, Masafumi Odaka "Focused Review: Fe-type nitrile hydratase"Journal of Inorganic Biochemistry 2001, Volume 83, Issue 4, February 2001, Pages 247–253. doi:10.1016/S0162-0134(00)00171-9