Cysteine sulfinic acid

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Cysteine sulfinic acid
Skeletal formula 3-Sulfino-L-alanine.svg
Skeletal formula
Ball-and-stick model L-Cysteine-sulfinic-acid-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH cysteine+sulfinic+acid
PubChem CID
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 mark.svgN
    Key: ADVPTQAUNPRNPO-REOHCLBHSA-N X mark.svgN
  • 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 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]

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). Degradation of Cysteine to Taurine.svg
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]

References

  1. ↑ Hayward, Laura; Baud, Matthias G. J. (2025). "Cysteine sulfinic acid and sulfinylated peptides". RSC Chemical Biology. 6 (7): 1019–1033. doi:10.1039/D5CB00040H. PMC   12093155 . PMID   40406162.
  2. ↑ 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.
  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. ↑ Akter, Salma; Fu, Ling; Jung, Youngeun; Conte, Mauro Lo; Lawson, J. Reed; Lowther, W. Todd; Sun, Rui; Liu, Keke; Yang, Jing; Carroll, Kate S. (2018). "Chemical proteomics reveals new targets of cysteine sulfinic acid reductase". Nature Chemical Biology. 14 (11): 995–1004. doi:10.1038/s41589-018-0116-2. PMC   6192846 . PMID   30177848.
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