Cysteine sulfinic acid

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Cysteine sulfinic acid
Skeletal formula
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
IUPHAR/BPS
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 ☒N
    Key: ADVPTQAUNPRNPO-REOHCLBHSA-N ☒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
  • 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 sulfinic acid is the

post-translationally. Peptides containing the cysteine sulfinic acid residue are substrates for cysteine sulfinic acid reductase.[1]

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