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 compound → a 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
Standard Gibbs Free Energy of Formation (ΔfG'° in kcal/mol): -119.73535 [Latendresse13]
Reactions known to consume the compound:
Reactions known to produce the compound:
Reactions known to both consume and produce the compound:
In Reactions of unknown directionality:
This compound has been characterized as an alternative substrate of the following enzymes: cysteine sulfinic acid decarboxylase, aspartate transaminase, transport of glutamate, sulfinoalanine decarboxylase
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
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
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