Misplaced Pages

Hypotaurine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Hypotaurine
Skeletal formula of Hypotaurine
Ball-and-stick model of the hypotaurine zwitterion
Names
Preferred IUPAC name 2-Aminoethane-1-sulfinic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.155.825 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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 , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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. It is an osmolyte with antioxidant properties.

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.

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

References

  1. 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.
  2. Paul H. Yancey (2005). "Organic osmolytes as compatible, metabolic and counteracting cytoprotectants in high osmolarity and other stresses". Journal of Experimental Biology. 208 (15): 2819–2830. doi:10.1242/jeb.01730. PMID 16043587.
  3. 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.
Neurotransmitters
Amino acid-derived
Major excitatory /
inhibitory systems
Glutamate system
GABA system
Glycine system
GHB system
Biogenic amines
Monoamines
Trace amines
Others
Neuropeptides
Lipid-derived
Endocannabinoids
Neurosteroids
Nucleobase-derived
Nucleosides
Adenosine system
Vitamin-derived
Miscellaneous
Cholinergic system
Gasotransmitters
Candidates
Glycine receptor modulators
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Ionotropic glutamate receptor modulators
Stub icon

This drug article relating to the nervous system is a stub. You can help Misplaced Pages by expanding it.

Categories: