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Homocysteic acid

From Wikipedia, the free encyclopedia
Homocysteic acid
L-Homocysteic acid
Names
IUPAC name
(2S)-2-Amino-4-sulfobutanoic acid
Other names
Homocysteate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1
    Key: VBOQYPQEPHKASR-VKHMYHEASA-N
  • C(CS(=O)(=O)O)[C@@H](C(=O)O)N
Properties
C4H9NO5S
Molar mass183.18 g·mol−1
Appearancewhite or colorless solid
Melting point261 °C (502 °F; 534 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Homocysteic acid is theorganosulfur compound with the formulaHO3SCH2CH2CH(NH2)CO2H. A white solid, it issulfonic acid-containingnon-proteinogenic amino acid. It is ananalog ofglutamic acid and is a potentNMDAreceptor agonist.[1][2] It is related tohomocysteine, a by-product ofmethionine metabolism.

Homocysteic acid is prepared by the oxidation ofhomocystine with aqueousbromine.[3]

References

[edit]
  1. ^Grandes, P; Kq, KQD; Morino, P; Cuénod, M; Streit, P (1991). "Homocysteate, an Excitatory Transmitter Candidate Localized in Glia".The European Journal of Neuroscience.3 (12):1370–1373.doi:10.1111/j.1460-9568.1991.tb00070.x.PMID 12106235.S2CID 23139077.
  2. ^Yuzaki, M; Connor, JA (1999). "Characterization of L-homocysteate-induced currents in Purkinje cells from wild-type and NMDA receptor knockout mice".Journal of Neurophysiology.82 (5):2820–6.doi:10.1152/jn.1999.82.5.2820.PMID 10561449.S2CID 16073533.
  3. ^Watkins, J. C. (1962). "The Synthesis of Some Acidic Amino Acids Possessing Neuropharmacological Activity".Journal of Medicinal and Pharmaceutical Chemistry.5 (6):1187–1199.doi:10.1021/jm01241a010.PMID 14056452.
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor

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