L-AP4 | 23052-81-5

L-AP4 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
InChI	1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChIKey	DDOQBQRIEWHWBT-VKHMYHEASA-N
SMILES	N[C@@H](CCP(O)(O)=O)C(O)=O
CAS DataBase Reference	23052-81-5(CAS DataBase Reference)
FDA UNII	C8M58SS68H
UNSPSC Code	12352202
NACRES	NA.32

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P261-P280a-P304+P340-P305+P351+P338-P405-P501a

PPE

dust mask type N95 (US), Eyeshields, Gloves

Hazard Codes

Xi

Risk Statements

36/37/38

Safety Statements

26-36

WGK Germany

3

RTECS

ES7191700

Storage Class

11 - Combustible Solids

NFPA 704

	0
2		0

L-AP4 price More Price(41)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	A7929	L-(+)-2-Amino-4-phosphonobutyric acid optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)	23052-81-5	0.5mg	$114	2026-04-30	Buy
Sigma-Aldrich	SRP3299	GDF-5 mouse recombinant, expressed in E. coli, ≥98% (SDS-PAGE), ≥98% (HPLC)		50 μg	$392	2026-04-30	Buy
Sigma-Aldrich	SRP4580	BMP-14 (GDF-5/CDMP-1) human recombinant, expressed in E. coli, ≥98% (SDS-PAGE), ≥98% (HPLC)		50 μg	$356	2025-07-31	Buy
Sigma-Aldrich	SRP4667	GDF-5 human recombinant, expressed in E. coli, ≥95% (SDS-PAGE), ≥95% (HPLC)	23052-81-5	50μG	$316	2022-05-15	Buy
Sigma-Aldrich	165300	L-(+)-2-Amino-4-phosphonobutyric Acid	23052-81-5	1mg	$88.3	2022-05-15	Buy

Product number	Packaging	Price	Buy
A7929	0.5mg	$114	Buy
SRP3299	50 μg	$392	Buy
SRP4580	50 μg	$356	Buy
SRP4667	50μG	$316	Buy
165300	1mg	$88.3	Buy

L-AP4 Chemical Properties, Uses, Production

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 synthesis

Synthesis of L-AP4 from (S)-2-Amino-4-(diethoxyphosphoryl)butanoic acid

L-AP4 Preparation Products And Raw materials

Raw materials

Glycine, N-[(1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]-, ethyl ester, [N(E)]- (S)-2-Amino-4-(diethoxyphosphoryl)butanoic acid D-AP4 Diethyl vinylphosphonate

Preparation Products

L-AP4 Suppliers

Global Suppliers ( 127)

Supplier	Tel	Email	Country	ProdList	Advantage
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
3B Pharmachem (Wuhan) International Co.,Ltd.	18930552037	3bsc@sina.com	China	15813	69
Wuhan Chemwish Technology Co., Ltd	86-027-67849912	sales@chemwish.com	China	35884	56
Ascent Scientific	4401179829988	customerservice@ascentscientific.co.uk	United Kingdom	279	60
Shanghai Sinch Parmaceuticals Tech. Co. Ltd.	+86-21-54098501	sales@sinch.com.cn	China	11592	64
Spectrum Chemical Manufacturing Corp.	021-021-021-67601398-809-809-809 15221380277	marketing_china@spectrumchemical.com	China	9643	60
BOC Sciences	1-631-485-4226; 16314854226	info@bocsci.com	United States	9920	65
Shanghai Balmxy Pharmaceutical Co., Ltd	021-24206007 13764915196	sales@balmxy.com	China	6959	55
Sigma-Aldrich	021-61415566 800-8193336	orderCN@merckgroup.com	China	51389	80
Shanghai Lollane Biological Technology Co.,Ltd.	021-52996696，15000506266 15000506266		China	4859	55

Supplier	Advantage
J & K SCIENTIFIC LTD.	76
3B Pharmachem (Wuhan) International Co.,Ltd.	69
Wuhan Chemwish Technology Co., Ltd	56
Ascent Scientific	60
Shanghai Sinch Parmaceuticals Tech. Co. Ltd.	64
Spectrum Chemical Manufacturing Corp.	60
BOC Sciences	65
Shanghai Balmxy Pharmaceutical Co., Ltd	55
Sigma-Aldrich	80
Shanghai Lollane Biological Technology Co.,Ltd.	55

View Latest Price from L-AP4 manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-07-10	L-AP4 23052-81-5	$198.00-589.00			10g	TargetMol Chemicals Inc.
2026-06-30	L-AP4 23052-81-5		1KG	98%	1000kg	Shaanxi Dideu New Materials Co. Ltd
2021-08-12	L-AP4 23052-81-5	$10.00-15.00	1KG	99%+ HPLC		Zhuozhou Wenxi import and Export Co., Ltd

L-AP4
23052-81-5
$198.00-589.00
TargetMol Chemicals Inc.

L-AP4
23052-81-5
$0.00
98%
Shaanxi Dideu New Materials Co. Ltd

L-AP4
23052-81-5
$10.00-15.00
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

23052-81-5 (L-AP4) Related Search:

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L-AP4 L(+)-2-AMINO-4-PHOSPHONOBUTANOIC ACID L-(+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID L-(+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID (L-AP4) L(+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID 97% (2S)-2-Amino-4-phosphonobutyric acid (S)-4-Phosphono-2-aminobutanoic acid (S)-4-Phosphono-2-aminobutyric acid L-APB L(+)-2-Amino-4-phosphonobutyric acid,97% (S)-2-aMino-4-phosphonobutanoic acid GDF-5 human SYNS2 BMP-14 (GDF-5/CDMP-1) human BMP-14/ CDMP-1 GDF-5 mouse Anti-GDF5 (C-terminal) antibody produced in rabbit CDMP1 L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) 2-ammonio-4-phosphonatobutanoate L-(+)-2-Amino-4-phosphonobutyric Acid - CAS 23052-81-5 - Calbiochem (2S)-2-amino-4-phosphonobutanoic acid Butanoic acid, 2-amino-4-phosphono-, (2S)- L-AP4, group III mGlu agonist L-AP4 (mM/ml), group III mGlu agonist L-(+)-2-Amino-4-phosphonobutyric acid BDA1C SYM1B L-(+)-2-Amino-4-phosphonobutyric acid[A7929] GDF5 (2S)-2-Amino-4-phosphonobutanoic acid (ACI) 23052-81-5 C4H10NO5P mGluR4 and mGluR6 metabotropic glutamate receptor agonist. Glutamate receptor Glutamate