All Photos(1)
Synonym(s):
β-N-Oxalo-L-α,β-diaminopropionic acid, β-N-Oxalyl-L-α,β-diaminopropionate, 3-[(Carboxycarbonyl)amino]-L-alanine, BOAA, Dencichin, Dencichine, Nβ-Oxalylamino-L-alanine, ODAP
Empirical Formula (Hill Notation):
C5H8N2O5
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
optical activity
[α]/D -17 to -23°, c = 0.5 (Solvent: 4N HCl)
color
white to beige
solubility
0.1 M HCl: 2 mg/mL, clear (warmed)
storage temp.
2-8°C
SMILES string
OC([C@@H](N)CNC(C(O)=O)=O)=O
InChI
1S/C5H8N2O5/c6-2(4(9)10)1-7-3(8)5(11)12/h2H,1,6H2,(H,7,8)(H,9,10)(H,11,12)/t2-/m0/s1
InChI key
NEEQFPMRODQIKX-REOHCLBHSA-N
Biochem/physiol Actions
β-ODAP is a potent inhibitor of HIF-prolyl hydroxylase-2 (PHD-2) that induces HIF dependent HRE (hypoxia response element) in normoxic conditions. β-ODAP is an analog of glutamic acid present in Lathyrus sativus (grass pea) that activates AMPA receptors. β-ODAP causes neurolathyrism upon prolonged consumption of L. sativus seeds.
β-ODAP is considered more neurotoxic than α-ODAP, thus during food processing, its conversion to α isomer is essential. β-ODAP exhibits its neurotoxicity via the activation of metabotropic glutamatergic receptor.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Ravi Kumar Eslavath et al.
European journal of pharmacology, 791, 405-411 (2016-10-30)
Hypoxia inducible factor (HIF)-1α, a subunit of HIF transcription factor, regulates cellular response to hypoxia. In normoxic conditions, it is hydroxylated by prolyl hydroxylase (PHD)-2 and targeted for proteosomal degradation. Drugs which inhibit PHD-2 have implications in conditions arising from
Kuniko Kusama-Eguchi et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 67, 113-122 (2014-03-04)
Neurolathyrism is a motor neuron (MN) disease caused by β-N-oxalyl-L-α,β-diaminopropionic acid (L-β-ODAP), an AMPA receptor agonist. L-β-ODAP caused a prolonged rise of intracellular Ca(2+) ([Ca(2+)]i) in rat spinal cord MNs, and the [Ca(2+)]i accumulation was inversely proportional to the MN's
Medical Toxicology of Natural Substances: Foods, Fungi, Medicinal Herbs, Plants, and Venomous Animals (2012)
Nalini Jammulamadaka et al.
Journal of neurochemistry, 118(2), 176-186 (2011-05-11)
β-N-Oxalyl-L-α,β-diaminopropionic acid (l-ODAP) an α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptor agonist activates protein kinase C in white leghorn chick brain. The current study focuses on the protein kinase C downstream signaling targets associated with L-ODAP excitotoxicity in SK-N-MC human neuroblastoma cells
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