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Cysteine sulfinic acid

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.

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. Proteins containing this residue are found at the active site of some nitrile hydratases.

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

References

References

  1. (2025). "Cysteine sulfinic acid and sulfinylated peptides". RSC Chemical Biology.
  2. Sumizu K. (1962). "Oxidation of hypotaurine in rat liver". Biochim. Biophys. Acta.
  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
  4. (2018). "Chemical proteomics reveals new targets of cysteine sulfinic acid reductase". Nature Chemical Biology.
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alpha-amino-acids sulfur-amino-acids sulfinic-acids
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