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Cysteic acid

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l-Cysteic acid
L-Cysteic acid
Ball-and-stick model
Names
IUPAC name (R)-2-Amino-3-sulfopropanoic acid
Other names 3-Sulfo-l-alanine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.265.539 Edit this at Wikidata
EC Number
  • 207-861-3
MeSH Cysteic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1Key: XVOYSCVBGLVSOL-REOHCLBHSA-N
  • InChI=1/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
SMILES
  • C(C(C(=O)O)N)S(=O)(=O)O
Properties
Chemical formula C3H7NO5S
Molar mass 169.15 g·mol
Appearance White crystals or powder
Melting point Decomposes around 272 °C
Solubility in water Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Cysteic acid also known as 3-sulfo-l-alanine is the organic compound with the formula HO3SCH2CH(NH2)CO2H. It is often referred to as cysteate, which near neutral pH takes the form O3SCH2CH(NH3)CO2.

It is an amino acid generated by oxidation of cysteine, whereby a thiol group is fully oxidized to a sulfonic acid/sulfonate group. It is further metabolized via 3-sulfolactate, which converts to pyruvate and sulfite/bisulfite. The enzyme L-cysteate sulfo-lyase catalyzes this conversion. Cysteate is a biosynthetic precursor to taurine in microalgae. By contrast, most taurine in animals is made from cysteine sulfinate.

References

  1. Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C259. ISBN 0-8493-0462-8..
  2. Tevatia, Rahul; Allen, James; Rudrappa, Deepak; White, Derrick; Clemente, Thomas E.; Cerutti, Heriberto; Demirel, Yaşar; Blum, Paul (2015-05-01). "The taurine biosynthetic pathway of microalgae". Algal Research. 9: 21–26. doi:10.1016/j.algal.2015.02.012. ISSN 2211-9264.
  3. Cook, Alasdair M.; Denger, Karin; Smits, Theo H. M. (2006). "Dissimilation of C3-Sulfonates". Archives of Microbiology. 185 (2): 83–90. doi:10.1007/s00203-005-0069-1. PMID 16341843. S2CID 28030645.


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