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CAS 79055-68-8

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(-)-2-Amino-5-phosphonovaleric acid

Description:
(-)-2-Amino-5-phosphonovaleric acid, commonly referred to as APV, is a synthetic amino acid derivative that acts as a selective antagonist of the N-methyl-D-aspartate (NMDA) receptor, which is a subtype of glutamate receptor in the central nervous system. This compound is characterized by its phosphonate group, which contributes to its biological activity and solubility in aqueous solutions. APV is often used in neuropharmacological research to study synaptic transmission and plasticity, particularly in the context of learning and memory. The stereochemistry of APV is significant, as the (-) enantiomer exhibits the desired antagonistic properties, while the (+) form does not. In terms of physical properties, APV is typically a white crystalline solid, soluble in water, and has a relatively low molecular weight. Its ability to modulate NMDA receptor activity makes it a valuable tool in both experimental and therapeutic contexts, particularly in understanding neurodegenerative diseases and conditions associated with excitotoxicity.
Formula:C5H12NO5P
InChI:InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1
InChI key:InChIKey=VOROEQBFPPIACJ-SCSAIBSYSA-N
SMILES:C(C[C@H](C(O)=O)N)CP(=O)(O)O
Synonyms:
  • 5-Phosphono-D-norvaline
  • D-2-Amino-5-phosphonovaleric acid
  • (-)-2-Amino-5-phosphonopentanoic acid
  • (-)-2-Amino-5-phosphonovaleric acid
  • D-Norvaline, 5-phosphono-
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