Cysteic acid

l-Cysteic acid
Names


IUPAC name (R)-2-Amino-3-sulfopropanoic acid
Other names 3-Sulfo-l-alanine
Identifiers
CAS Number	13100-82-8 (D/L)^Y 35554-98-4 (D)^Y 498-40-8 (L)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17285^Y
ChemSpider	65718^Y
DrugBank	DB03661^Y
ECHA InfoCard	100.265.539
EC Number	207-861-3
MeSH	Cysteic+acid
PubChem CID	25701
UNII	A3OGP4C37W (D/L)^Y YWB11Z1XEI (D)^Y M6W2DJ6N5K (L)^Y
CompTox Dashboard (EPA)	DTXSID40862048
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/s1^Y Key: XVOYSCVBGLVSOL-REOHCLBHSA-N^Y 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^[1]
Chemical formula	C₃H₇NO₅S
Molar mass	169.15 g·mol⁻¹
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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

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References

^ 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..
^ 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.
^ 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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This page was last edited on 10 January 2024, at 17:55

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