L-2-AMINO-4-SULFOBUTYRIC ACID

Names

[ CAS No. ]:
14857-77-3

[ Name ]:
L-2-AMINO-4-SULFOBUTYRIC ACID

[Synonym ]:
L-2-Amino-4-sulfobutyric acid
(2S)-2-amino-4-sulfobutanoic acid

Biological Activity

[Description]:

L-Homocysteic acid (L-HCA) is an endogenous excitatory amino acid that acts as a NMDA receptor agonist (EC50: 14 μM). L-Homocysteic acid is neurotoxic, and can be used in the research of neurological disorders[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR
Research Areas >> Neurological Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

NMDA Receptor:14 μM (EC50)


[In Vitro]

L-Homocysteic acid activates NMDA receptor with an EC50 value of 14 μM[1]. L-Homocysteic acid (100 μM) induces large currents (1.8 nA) that is insensitive to the NMDA receptor-antagonist mixture in Purkinje cells[1]. L-Homocysteic acid (250 μM, 30 min) potently induces an acute excitotoxic reaction in ex vivo chick embryo retina[2]. L-Homocysteic acid (0-2 mM, 48 h) induces a concentration-dependent neurotoxic effect in rat primary neurons[3].

[In Vivo]

L-Homocysteic acid (intraperitoneal injection, 4-11 mmol/kg) elicits seizures in rats during early postnatal development[4]. L-Homocysteic acid (intraperitoneal injection, 100-1500 mg/kg) partially substitutes for NMDA, producing maximum values of 61-67% NMDA-lever responding at doses of 1000 and 560 mg/kg, respectively in Sprague-Dawley rats[5]. Animal Model: Male albino rats of the Wistar strain[4] Dosage: 4, 5.5, 8, 11 mM/kg Administration: Intraperitoneal injection, daily for 14 days Result: Induced flexion seizures at 4 mmol/kg. Led to intense tail flicking, pivoting, and locomotion. Decreased ECoG (electrocorticograms) activity for 5-9 min.

[References]

[1]. M Yuzaki, et al. Characterization of L-homocysteate-induced currents in Purkinje cells from wild-type and NMDA receptor knockout mice. J Neurophysiol . 1999 Nov;82(5):2820-6.

[2]. J W Olney, et al. L-homocysteic acid: an endogenous excitotoxic ligand of the NMDA receptor. Brain Res Bull. 1987 Nov;19(5):597-602.

[3]. B Lockhart, et al. Inhibition of L-homocysteic acid and buthionine sulphoximine-mediated neurotoxicity in rat embryonic neuronal cultures with alpha-lipoic acid enantiomers. Brain Res. 2000 Feb 14;855(2):292-7.

[4]. P Mares, et al. Convulsant action of D,L-homocysteic acid and its stereoisomers in immature rats.

[5]. Katherine L Nicholson, et al. The discriminative stimulus effects of N-methyl-D-aspartate glycine-site ligands in NMDA antagonist-trained rats. Psychopharmacology (Berl). 2009 Apr;203(2):441-51.

Chemical & Physical Properties

[ Density]:
1.638g/cm3

[ Molecular Formula ]:
C4H9NO5S

[ Molecular Weight ]:
183.18300

[ Exact Mass ]:
183.02000

[ PSA ]:
126.07000

[ LogP ]:
0.45730

[ Index of Refraction ]:
1.56

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2922499990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922499990

[ Summary ]:
HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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