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AP5

In this article we are going to address the topic of AP5 from a multidisciplinary perspective, with the aim of providing the reader with a comprehensive and analytical vision of this topic. To do this, we will take a tour of different aspects related to AP5, such as its origin, evolution, impact on current society, and possible future scenarios. In addition, we will focus on the importance of AP5 in various fields of knowledge, as well as its relevance in people's daily lives. Through this article, we aim to generate a deep and enriching reflection on AP5, thus promoting greater understanding and appreciation for this topic that is so relevant today.

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This article is about the chemical compound. For the Star Wars Rebels TV series character, see AP-5.
AP5
Names
Preferred IUPAC name
(2R)-2-Amino-5-phosphonopentanoic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.150.904 Edit this at Wikidata
UNII
  • 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 checkY
    Key: VOROEQBFPPIACJ-SCSAIBSYSA-N checkY
  • InChI=1/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
    Key: VOROEQBFPPIACJ-SCSAIBSYBE
  • O=P(O)(O)CCC(N)C(=O)O
Properties
C5H12NO5P
Molar mass 197.13 g/mol
Appearance white solid
Density 1.529 g/mL
Boiling point 482.1 °C (899.8 °F; 755.2 K)
Ammonium hydroxide, 50 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
☒N verify (what is checkY☒N ?)

AP5 (also known as APV, (2R)-amino-5-phosphonovaleric acid, or (2R)-amino-5-phosphonopentanoate) is a chemical compound used as a biochemical tool to study various cellular processes. It is a selective NMDA receptor antagonist that competitively inhibits the ligand (glutamate) binding site of NMDA receptors.[1] AP5 blocks NMDA receptors in micromolar concentrations (~50 μM).

AP5 blocks the cellular analog of classical conditioning in the sea slug Aplysia californica, and has similar effects on Aplysia long-term potentiation (LTP), since NMDA receptors are required for both.[2] It is sometimes used in conjunction with the calcium chelator BAPTA to determine whether NMDARs are required for a particular cellular process. AP5/APV has also been used to study NMDAR-dependent LTP in the mammalian hippocampus.[3]

In general, AP5 is very fast-acting within in vitro preparations, and can block NMDA receptor action at a reasonably small concentration. The active isomer of AP5 is considered to be the D configuration, although many preparations are available as a racemic mixture of D- and L-isomers. It is useful to isolate the action of other glutamate receptors in the brain, i.e., AMPA and kainate receptors.

AP5 can block the conversion of a silent synapse to an active one, since this conversion is NMDA receptor-dependent.

See also

References

  1. ^ Morris, RG (Sep 1989). "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". Journal of Neuroscience. 9 (9): 3040–57. PMID 2552039.
  2. ^ Cellular Analog of Differential Classical Conditioning in Aplysia: Disruption by the NMDA Receptor Antagonist DL-2-Amino-5-Phosphonovalerate
  3. ^ Gustafsson, B.; Wigström, H.; Abraham, W.C.; Huang, Y.Y. (March 1987). "Long-Term Potentiation in the Hippocampus Using Depolarizing Current Pulses as the Conditioning Stimulus to Single Volley Synaptic Potentials". Journal of Neuroscience. 7 (3): 774–780.
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