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Cysteine sulfinic acid

Chemical compound From Wikipedia, the free encyclopedia

Cysteine sulfinic acid is the organic compound with the nominal formula HO2SCH2CH(NH2)CO2H . It is a rare example of an amino acid bearing a sulfinic acid functional group. It is a white solid that is soluble in water. Like most natural amino acids, it is chiral, only the L-enantiomer occurs in nature, and it exists as the zwitterion at neutral pH. It is an intermediate in cysteine metabolism. It is not a coded amino acid, but is produced post-translationally.[1]

Quick facts Names, Identifiers ...
Cysteine sulfinic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
2-amino-3-sulfinopropanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.012.935 Edit this at Wikidata
KEGG
MeSH cysteine+sulfinic+acid
UNII
  • InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 X markN
    Key: ADVPTQAUNPRNPO-REOHCLBHSA-N X markN
  • 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
  • O=C(O)[C@@H](N)CS(=O)O
Properties
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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Cysteine 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).

Peptides containing the cysteine sulfinic acid residue are substrates for cysteine sulfinic acid reductase.[4]

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