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) ; 35554-98-4 (D) ; 498-40-8 (L) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17285 ;
ChemSpider	65718 ;
DrugBank	DB03661 ;
ECHA InfoCard	100.265.539
EC Number	207-861-3;
MeSH	Cysteic+acid
PubChem CID	25701;
UNII	A3OGP4C37W (D/L) ; YWB11Z1XEI (D) ; M6W2DJ6N5K (L) ;
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 Key: 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[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).
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	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 not a biosynthetic precursor to taurine, which is derived from cysteine sulfinate.[2]

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..
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.CS1 maint: uses authors parameter (link)

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[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] 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.CS1 maint: uses authors parameter (link)