2-amino-5-phosphonovaleric acid

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Structural formula
Structure of 2-amino-5-phosphonovaleric acid
Structural formula of the ( R ) isomer
General
Surname 2-amino-5-phosphonovaleric acid
other names
  • ( R ) -2-amino-5-phosphono-pentanoic acid
  • APV
  • AP5
Molecular formula C 5 H 12 NO 5 P
Brief description

colorless crystalline solid

External identifiers / databases
CAS number 79055-68-8
EC number 622-112-4
ECHA InfoCard 100.150.904
PubChem 135342
ChemSpider 119225
Wikidata Q209309
properties
Molar mass 197.1 g mol −1
Physical state

firmly

solubility

Easily soluble in cold water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Amino-5-phosphonovaleric acid ( APV or AP5 for short ) is a synthetic, non-proteinogenic amino acid .

APV is a selective NMDA receptor antagonist that competitively inhibits this receptor even in small doses . The D - enantiomer of this amino acid is regarded as the biologically active isomer .

Sample of APV

APV was developed by Jeff Watkins and Harry Olverman .

Individual evidence

  1. ↑ a b Data sheet D - (-) - 2-Amino-5-phosphonopentanoic Acid (PDF) from Calbiochem, accessed on December 8, 2015.
  2. ↑ a b Data sheet D (-) - 2-Amino-5-phosphonopentanoic acid from Sigma-Aldrich , accessed on March 19, 2011 ( PDF ).
  3. ^ RG Morris: Synaptic plasticity and learning: selective impairment of learning rats and blockade of long-term potentiation in vivo by the N-methyl-D-aspartate receptor antagonist AP5. In: The Journal of neuroscience: the official journal of the Society for Neuroscience. Volume 9, Number 9, September 1989, pp. 3040-3057, PMID 2552039 .
  4. ↑ HJ Olverman, AW Jones, JC Watkins: L-glutamate has higher affinity than other amino acids for [3H] -D-AP5 binding sites in rat brain membranes. In: Nature. Volume 307, Number 5950, 1984 Feb 2-8, pp. 460-462, PMID 6141527 .
  5. ^ J. Davies, JC Watkins: Actions of D and L forms of 2-amino-5-phosphonovalerate and 2-amino-4-phosphonobutyrate in the cat spinal cord. In: Brain research. Volume 235, Number 2, March 1982, pp. 378-386, PMID 6145492 .

literature