2-amino-5-phosphonovaleric acid
Structural formula | |||||||||||||||||||
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Structural formula of the ( R ) isomer | |||||||||||||||||||
General | |||||||||||||||||||
Surname | 2-amino-5-phosphonovaleric acid | ||||||||||||||||||
other names |
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Molecular formula | C 5 H 12 NO 5 P | ||||||||||||||||||
Brief description |
colorless crystalline solid |
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properties | |||||||||||||||||||
Molar mass | 197.1 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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solubility |
Easily soluble in cold water |
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safety instructions | |||||||||||||||||||
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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 .
APV was developed by Jeff Watkins and Harry Olverman .
Individual evidence
- ↑ a b Data sheet D - (-) - 2-Amino-5-phosphonopentanoic Acid (PDF) from Calbiochem, accessed on December 8, 2015.
- ↑ a b Data sheet D (-) - 2-Amino-5-phosphonopentanoic acid from Sigma-Aldrich , accessed on March 19, 2011 ( PDF ).
- ^ 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 .
- ↑ 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 .
- ^ 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
- GG Murphy, DL Glanzman: Cellular analog of differential classical conditioning in Aplysia: disruption by the NMDA receptor antagonist DL -2-amino-5-phosphonovalerate. In: The Journal of neuroscience Volume 19, Number 23, December 1999, pp. 10595-10602, PMID 10575055 .