All Photos(1)

Documents

A7929

L-(+)-2-Amino-4-phosphonobutyric acid

Name: <SC>L</SC>-(+)-2-Amino-4-phosphonobutyric acid
Brand: SIGMA

optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)

Sign Into View Organizational & Contract Pricing

All Photos(1)

Synonym(s):

L-AP-4, L-AP4

Empirical Formula (Hill Notation):

C₄H₁₀NO₅P

CAS Number:

23052-81-5

Molecular Weight:

183.10

MDL number:

MFCD00083244

PubChem Substance ID:

24891296

NACRES:

NA.32

form

powder

optical purity

optical purity: ≥95% (HPLC, Marfey′s reagent)

SMILES string

N[C@@H](CCP(O)(O)=O)C(O)=O

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

InChI key

DDOQBQRIEWHWBT-VKHMYHEASA-N

Gene Information

human ... GRM1(2911) , GRM2(2912) , GRM3(2913) , GRM4(2914) , GRM6(2916) , GRM7(2917) , GRM8(2918)
rat ... Grm1(24414) , Grm2(24415) , Grm4(24417) , Grm5(24418) , Grm6(24419) , Grm7(81672)

Looking for similar products? Visit Product Comparison Guide

Biochem/physiol Actions

mGluR₄ and mGluR₆ metabotropic glutamate receptor agonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

How to Find the Product Number

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503

Product Number

25G

Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

How to Find a Lot/Batch Number for COA

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').
For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').
For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.

Chelliah Selvam et al.

Journal of medicinal chemistry, 53(7), 2797-2813 (2010-03-12)

(R)-PCEP (3-amino-3-carboxypropyl-2'-carboxyethyl phosphinic acid, 1), a new metabotropic glutamate receptor 4 (mGlu4R) agonist, was discovered in a previously reported virtual screening. The (S)-enantiomer and a series of derivatives were synthesized and tested on recombinant mGlu4 receptors. A large number of

Activity-dependent synaptic integration and modulation of bilateral excitatory inputs in an auditory coincidence detection circuit.

Yong Lu et al.

The Journal of physiology, 596(10), 1981-1997 (2018-03-25)

Binaural excitatory inputs to coincidence detection neurons in nucleus laminaris (NL) play essential roles in interaural time difference coding for sound localization. Here, we show that the two excitatory inputs are physiologically nearly completely segregated. Synaptic integration shows linear summation

L-(+)-2-Amino-4-thiophosphonobutyric acid (L-thioAP4), a new potent agonist of group III metabotropic glutamate receptors: increased distal acidity affords enhanced potency.

Chelliah Selvam et al.

Journal of medicinal chemistry, 50(19), 4656-4664 (2007-08-29)

L-2-Amino-4-phosphonobutyric acid (l-AP4), l-2-amino-4-thiophosphonobutyric acid (l-thioAP4), and l-2-amino-4-(hydroxy)phosphinylbutyric acid (desmethylphosphinothricin, DMPT) were synthesized from protected vinylglycine. They were tested as agonists at group III metabotropic glutamate receptors (mGluR) along with phosphinothricin (PT). DMPT and PT display a much lower potency

LRIT3 is Required for Nyctalopin Expression and Normal ON and OFF Pathway Signaling in the Retina.

Nazarul Hasan et al.

eNeuro, 7(1) (2020-01-22)

The first retinal synapse, photoreceptor→bipolar cell (BC), is both anatomically and functionally complex. Within the same synaptic region, a change in presynaptic glutamate release is sensed by both ON BCs (DBCs) via the metabotropic glutamate receptor 6 (mGluR6), and OFF

Synthesis and biological evaluation of 1-amino-2-phosphonomethylcyclopropanecarboxylic acids, new group III metabotropic glutamate receptor agonists.

Pauline Sibille et al.

Journal of medicinal chemistry, 50(15), 3585-3595 (2007-07-03)

Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays

View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service