Cysteic acid

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.

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
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.265.539
EC Number
  • 207-861-3
MeSH Cysteic+acid
UNII
  • 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/s1 checkY
    Key: XVOYSCVBGLVSOL-REOHCLBHSA-N checkY
  • 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
  • C(C(C(=O)O)N)S(=O)(=O)O
Properties[1]
C3H7NO5S
Molar mass 169.15 g·mol−1
Appearance White crystals or powder
Melting point Decomposes around 272 °C
Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2] By contrast, most taurine in animals is made from cysteine sulfinate.[3]

References

  1. Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: 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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