L-AP4 Chemical Properties

Melting point:

207-215 °C

Boiling point:

491.7±55.0 °C(Predicted)

Density 

1.628±0.06 g/cm3(Predicted)

storage temp. 

0-6°C

solubility 

H2O : 50 mg/mL (273.07 mM; Need ultrasonic)

pka

2.19±0.10(Predicted)

form 

solid

color 

White

biological source

human

Water Solubility 

Soluble to 5 mM in water and to 100 mM in 1eq. NaOH

Sensitive 

Light Sensitive

CAS DataBase Reference

23052-81-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

ES7191700

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-AP4 Usage And Synthesis

Description

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC₅₀ = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Chemical Properties

white to off-white crystalline powder

Uses

Metabotropic glutamate receptors (mGluR) function to modulate excitatory synaptic transmission in the brain. Eight subtypes (1-8) and multiple splice variants of the mGluR have been identified and grouped based on their pharmacological properties. Group I mGluRs (subtypes 1 and 5) activate the phosphatidyl inositol pathway, while Group II (2 and 3) and Group III (4, 6, 7, and 8) inhibit adenylyl cyclase. L-AP4, an analog of L-glutamic acid, is a selective Group III mGluR agonist that functions presynaptically to suppress glutamate release (IC50 = 2.5 μM). L-AP4 has been shown to depress synaptic transmission in glutamatergic pathways in the hippocampus, olfactory bulb, and retina as well as act as an agonist at the quisqualate-sensitized AP6 site in hippocampus.

Uses

L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) is a mGluR-4/6 receptor agonist.

Definition

ChEBI: (2S)-2-amino-4-phosphonobutanoic acid is a non-proteinogenc L-alpha-amino acid that is L-alpha-aminobutyric acid in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). It has a role as a metabotropic glutamate receptor agonist. It is a non-proteinogenic L-alpha-amino acid and a member of phosphonic acids.

Biological Activity

Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™ .

storage

Room temperature

Description

GDF5 Mouse Recombinant produced in E.coli is a non-glycosylated disulfide linked homodimer containing 2 chains of 120 amino acids and having a molecular mass of 27.2kDa.
The GDF-5 is purified by proprietary chromatographic techniques.

Source

Escherichia Coli

Background

GDF-5 is a member of the bone morphogenetic protein (BMP) family and the TGF-beta superfamily. This group of proteins is characterized by a polybasic proteolytic processing site which is cleaved to produce a mature protein containing seven conserved cysteine residues. The members of this family are regulators of cell growth and differentiation in both embryonic and adult tissues. Mutations in this gene are associated with acromesomelic dysplasia, Hunter-Thompson type; brachydactyly, type C; and chondrodysplasia, Grebe type. These associations confirm that the gene product plays a role in skeletal development.

References

[1] THOMSEN C. The l-AP4 receptor[J]. General Pharmacology-the Vascular System, 1997, 29 2: Pages 151-158. DOI: 10.1016/s0306-3623(96)00417-x
[2] R.H. EVANS. THE EFFECTS OF A SERIES OF ω-PHOSPHONIC α-CARBOXYLIC AMINO ACIDS ON ELECTRICALLY EVOKED AND EXCITANT AMINO ACID-INDUCED RESPONSES IN ISOLATED SPINAL CORD PREPARATIONS[J]. British Journal of Pharmacology, 1982, 75 1: 65-75. DOI: 10.1111/j.1476-5381.1982.tb08758.x
[3] I. RYZHOVA. Metabotropic glutamate receptors in mechanisms of plasticity of the central nervous system in the honeybee Apis mellifera[J]. Journal of Evolutionary Biochemistry and Physiology, 2010, 46 1: 251-258. DOI: 10.1134/s002209301003004x

L-AP4(23052-81-5)Related Product Information

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• 4-PHOSPHONOBUTYRIC ACID
• 3-Aminopropylphosphonic acid
• (S)-2-Amino-2-methyl-4-phosphonobutanoic acid
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• L-AP4
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