Hypotaurine

Hypotaurine
Names
	IUPAC name 2-Aminoethanesulfinic acid
Identifiers
CAS Number	300-84-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:57853 ;
ChemSpider	96959 ;
ECHA InfoCard	100.155.825
KEGG	C00519 ;
PubChem CID	107812;
UNII	5L08GE4332 ;
CompTox Dashboard (EPA)	DTXSID8075380 ;
	InChI InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5) Key: VVIUBCNYACGLLV-UHFFFAOYSA-N ; InChI=1/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5) Key: VVIUBCNYACGLLV-UHFFFAOYAM;
	SMILES O=S(O)CCN;
Properties
Chemical formula	C2H7NO2S
Molar mass	109.15 g/mol
	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

Hypotaurine is a sulfinic acid that is an intermediate in the biosynthesis of taurine. Like taurine, it also acts as an endogenous neurotransmitter via action on the glycine receptors.[1] It is an osmolyte with antioxidant properties.[2]

Hypotaurine is derived from cysteine (and homocysteine). In mammals, the biosynthesis of hypotaurine from cysteine occurs in the pancreas. In the cysteine sulfinic acid pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase. Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine. Hypotaurine is enzymatically oxidized to yield taurine by hypotaurine dehydrogenase.[3]

Hypotaurine (3) is an intermediate in the conversion of cysteine (1) to taurine (4).

References

Kalir, Asher; Kalir, Henry H. "Biological activity of sulfinic acid derivatives" in Chemistry of Sulphinic Acids, Esters Their Derivatives Edited by Patai, Saul. Wiley, New York, 1990, pp. 665.
Paul H. Yancey (2005). "Organic osmolytes as compatible, metabolic and counteracting cytoprotectants in high osmolarity and other stresses". Journal of Experimental Biology. 208: 2819–2830. doi:10.1242/jeb.01730.
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.

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