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MetaCyc Compound: L-cysteate

Synonyms: L-cysteic acid, 3-sulfoalanine, 2-amino-3-sulfopropionic acid, (R)-cysteate, 3-sulfo-L-alanine, (2R)-2-amino-3-sulfopropanoic acid

Superclasses: an organosulfur compounda sulfonate

L-cysteate is a natural product first found in wool, and is an intermediate in cysteine metabolism involved in, for example, the synthesis of taurine in mammals [Weinstein88]. The compound also serves as a precursor of the cytophagal sulfolipid capnine [White84] and is found extracellularly in spiders' webs [Vollrath90].

Cysteate serves as a sole source of carbon and energy for the aerobic growth of bacteria [Stapley70, Rein05], as an electron acceptor for several sulfate-reducing bacteria [Lie96, Lie99], as an electron donor for some nitrate-reducing bacteria [Denger97, Mikosch99], and as the substrate for a fermentation in a sulfate-reducing bacterium [Laue97].

Chemical Formula: C3H6NO5S

Molecular Weight: 168.14 Daltons

Monoisotopic Molecular Weight: 170.01231806250001 Daltons

L-cysteate compound structure

SMILES: C(C([N+])C(=O)[O-])S(=O)(=O)[O-]

InChI: InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/p-1/t2-/m0/s1


Unification Links: ChEBI:58090, ChemSpider:5482600, HMDB:HMDB02757, KEGG:C00506, MetaboLights:MTBLC58090, PubChem:7140381

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -119.73535Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

sulfolactate degradation III :
L-cysteate + H2O → sulfite + pyruvate + ammonium + H+

Reactions known to produce the compound:

coenzyme M biosynthesis II :
3-phospho-L-serine + sulfite + H+L-cysteate + phosphate

Reactions known to both consume and produce the compound:

(R)-cysteate degradation , coenzyme M biosynthesis II , sulfolactate degradation III :
L-cysteate + 2-oxoglutarate ↔ 3-sulfopyruvate + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
sulfite + L-cysteine + H+ = hydrogen sulfide + L-cysteate
L-cysteate = sulfite + 2-aminoprop-2-enoate + 2 H+
L-cysteate + H+ = taurine + CO2

This compound has been characterized as an alternative substrate of the following enzymes: cysteine sulfinic acid decarboxylase, aspartate transaminase, transport of glutamate, sulfinoalanine decarboxylase

Revised 05-Oct-2010 by Caspi R, SRI International


Denger97: Denger K, Laue H, Cook AM (1997). "Anaerobic taurine oxidation: a novel reaction by a nitrate-reducing Alcaligenes sp." Microbiology 143 ( Pt 6);1919-24. PMID: 9202468

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Laue97: Laue, H., Denger, K., Cook, A. M. (1997). "Fermentation of cysteate by a sulfate-reducing bacterium." Arch Microbiol 168: 210-214.

Lie96: Lie TJ, Pitta T, Leadbetter ER, Godchaux W, Leadbetter JR (1996). "Sulfonates: novel electron acceptors in anaerobic respiration." Arch Microbiol 166(3);204-10. PMID: 8703197

Lie99: Lie TJ, Godchaux W, Leadbetter ER (1999). "Sulfonates as terminal electron acceptors for growth of sulfite-reducing bacteria (Desulfitobacterium spp.) and sulfate-reducing bacteria: effects of inhibitors of sulfidogenesis." Appl Environ Microbiol 65(10);4611-7. PMID: 10508097

Mikosch99: Mikosch CA, Denger K, Schafer EM, Cook AM (1999). "Anaerobic oxidations of cysteate: degradation via L-cysteate:2-oxoglutarate aminotransferase in Paracoccus pantotrophus." Microbiology 145 ( Pt 5);1153-60. PMID: 10376831

Rein05: Rein U, Gueta R, Denger K, Ruff J, Hollemeyer K, Cook AM (2005). "Dissimilation of cysteate via 3-sulfolactate sulfo-lyase and a sulfate exporter in Paracoccus pantotrophus NKNCYSA." Microbiology 151(Pt 3);737-47. PMID: 15758220

Stapley70: Stapley, E. O., Starkey, R. L. (1970). "Decomposition of cysteic acid and taurine by soil microorganisms." J Gen Microbiol 64: 77-84.

Vollrath90: Vollrath, F., Fairbrother, W. J., Williams, R. J. P., Tillinghast, E. K., Bernstein, D. T., Gallagher, K. S., Townley, M. A. (1990). "Compounds in the droplets of the orb spider's viscid spiral." Nature 345: 526-528.

Weinstein88: Weinstein CL, Griffith OW (1988). "Cysteinesulfonate and beta-sulfopyruvate metabolism. Partitioning between decarboxylation, transamination, and reduction pathways." J Biol Chem 263(8);3735-43. PMID: 3346220

White84: White RH (1984). "Biosynthesis of the sulfonolipid 2-amino-3-hydroxy-15-methylhexadecane-1-sulfonic acid in the gliding bacterium Cytophaga johnsonae." J Bacteriol 159(1);42-6. PMID: 6330048

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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