Chemistry:Homocysteic acid

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Homocysteic acid
L-Homocysteic acid.svg
L-Homocysteic acid
Names
IUPAC name
(2S)-2-Amino-4-sulfobutanoic acid
Other names
Homocysteate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
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).
Infobox references
Tracking categories (test):

Homocysteic acid is the organosulfur compound with the formula HO
3
SCH
2
CH
2
CH(NH
2
)CO
2
H
. 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. 
  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. 
  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.