Homocysteic acid

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 mass 183.18 g·mol−1
Appearance white or colorless solid
Melting point 261 °C (502 °F; 534 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Homocysteic acid is the organosulfur compound with the formula HO3SCH2CH2CH(NH2)CO2H. A white solid, it is sulfonic acid-containing non-proteinogenic amino acid. It is aanalog of glutamic acid and is a potent NMDA receptor agonist.[1][2] It is related to homocysteine, a by-product of methionine metabolism.

Homocysteic acid is prepared by the oxidation of homocystine with aqueous bromine.[3]

References

  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.


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