ChemicalBook CAS DataBase List 79055-68-8

79055-68-8

Name	D-AP5
CAS	79055-68-8
Molecular Formula	C5H12NO5P
MDL Number	MFCD00078839
Molecular Weight	197.13
MOL File	79055-68-8.mol

Synonyms

D-AP5 D-APV IF4G2 EIF4G2 (R)-AP-5 Death associated protein 5 (R)-2-Amino-5-phosphonovaleric acid (R)-5-Phosphono-2-aminovaleric acid D-2-AMINO-5-PHOSPHONOPENTANOIC ACID (2R)-2-Amino-5-phosphonovaleric acid D(-)-2-AMINO-5-PHOSPHONOPENTANOIC AC (R)-2-aMino-5-phosphonopentanoic acid D-(-)-2-AMINO-5-PHOSPHONOVALERIC ACID (2R)-2-aMMonio-5-phosphonatopentanoate D-(-)-2-AMINO-5-PHOSPHONOPENTANOIC ACID D(-)-2-Amino-5-phosphonovaleric acid hydrate D(-)-2-Amino-5-phosphonovaleric acid (D-AP5) Eukaryotic translation initiation factor 4 γ 2 D-(-)-2-AMINO-5-PHOSPHONOPENTANOIC ACID (D-AP5) Anti-EIF4G2, N-Terminal antibody produced in rabbit D(-)-AP-5, D(-)-APV, D-2-Amino-5-phosphonovaleric acid D(-)-2-Amino-5-phosphonovaleric acid hydrate,96%, (>98% ee)

Chemical Properties

Appearance	white fine crystalline powder
Melting point	approximate 233℃
Boiling point	482.1±55.0 °C(Predicted)
density	1.529±0.06 g/cm3(Predicted)
RTECS	RD2513000
storage temp.	Store at RT
solubility	Soluble to 100 mM in sterile
form	White solid
pka	2.46±0.10(Predicted)
color	White
Water Solubility	Soluble in water (100mM)
Sensitive	Light Sensitive
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
InChIKey	VOROEQBFPPIACJ-SCSAIBSYSA-N
SMILES	N[C@H](CCCP(O)(O)=O)C(O)=O

Safety Data

Hazard Codes	Xi
Risk Statements	36/37/38 less more
Safety Statements	26-36 less more
WGK Germany	3
Storage Class	11 - Combustible Solids

Hazard Information

Description

D-AP5 is a selective N-methyl-D-aspartate (NMDA) receptor antagonist (K_d = 1.4 μM) that competitively inhibits the glutamate binding site of NMDA receptors. Whereas D-AP5 is the active (−)-stereoisomer, its (+)-isomer (L-AP5) demonstrates considerably less potent NMDA receptor antagonist activity. AP5 has been widely used to study the activity of NMDA receptors particularly in regard to researching synaptic plasticity, learning, and memory.

Chemical Properties

white fine crystalline powder

Uses

A competitive NMDA antagonist

General Description

Active enantiomer of DL-2-amino-5-phosphonopentanoic acid (AP5) that is a commonly used competitive NMDA receptor antagonist.

Biological Activity

Widely used competitive NMDA antagonist. More active form of AP5. Also agonist at quisqualate-sensitized AP6 site where it is less potent than the L-isomer (L-(+)-2-Amino-5-phosphonopentanoic acid ). Also available as part of the Mixed NMDA Receptor Tocriset™ .

Biochem/physiol Actions

Product does not compete with ATP.

storage

Store at -20°C

References

[1] MORRIS R G. 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.[J]. Journal of Neuroscience, 1989, 9 9: 3040-3057.

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