3-(9-Anthryl)-L-alanine
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3-(9-Anthryl)-L-alanine

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Category
L-Amino Acids
Catalog number
BAT-007812
CAS number
100896-08-0
Molecular Formula
C17H15NO2
Molecular Weight
265.31
3-(9-Anthryl)-L-alanine
IUPAC Name
(2S)-2-amino-3-anthracen-9-ylpropanoic acid
Synonyms
3-Ala(9-anthryl)-OH; 3-(9-ANTHRYL)-L-ALANINE; (2S)-2-AMINO-3-(9-ANTHRYL)PROPANOIC ACID; 3-(9-anthryl)l-alanine
Appearance
Pale yellow solid
Purity
≥ 99.5% (Chiral HPLC)
Density
1.289±0.06 g/cm3 (Predicted)
Boiling Point
503.4±38.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H15NO2/c18-16(17(19)20)10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-9,16H,10,18H2,(H,19,20)/t16-/m0/s1
InChI Key
MRVJUNXMEDRMRO-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C=C3C=CC=CC3=C2CC(C(=O)O)N

3-(9-Anthryl)-L-alanine, due to its unique structure combining a 9-anthryl group and the amino acid L-alanine, finds significant applications in various scientific fields. One of the primary applications is in the field of molecular probes. The 9-anthryl group is known for its strong fluorescent properties, making this compound ideal for use as a fluorescent probe in biochemical assays. It can be used to label biological molecules and monitor their interactions and changes in real-time. This capability is crucial in studying protein folding, enzyme activities, and cellular processes, thereby enhancing our understanding of fundamental biological mechanisms.

Another key application of 3-(9-Anthryl)-L-alanine is in the development of sensors. The compound's fluorescence can be quenched or enhanced by various analytes, which makes it an excellent candidate for sensing applications. By incorporating this molecule into sensor systems, it is possible to detect the presence of metal ions, pH changes, and other environmental factors with high sensitivity and specificity. Such sensors are invaluable in environmental monitoring, medical diagnostics, and industrial process control, providing quick and accurate measurements essential for maintaining safety and efficiency.

3-(9-Anthryl)-L-alanine also plays a crucial role in pharmaceuticals, particularly in drug design and discovery. The alanine residue within the molecule can act as a mimic of natural peptides, which are often involved in key biological pathways. Coupled with the fluorescence of the anthryl group, it allows for the investigation of drug-protein interactions at a molecular level. This facilitates the identification and optimization of new therapeutic agents by enabling researchers to visualize and understand how potential drugs bind to and affect their targets. Consequently, this application holds promise for the development of more effective and targeted medications.

Lastly, the compound finds usage in material sciences, specifically in the design of organic electronic materials. The anthryl group contributes to the π-conjugated system, which is beneficial for the development of organic light-emitting diodes (OLEDs) and organic photovoltaic cells. The presence of the L-alanine group can improve solubility and processability, which are crucial for the fabrication of these materials. By incorporating 3-(9-Anthryl)-L-alanine into organic electronic devices, it is possible to achieve better performance, longevity, and efficiency, driving the advancement of sustainable and high-performance electronic components.

1.Effects of lipid structure on energy transfer from carbazolyl to anthryl groups in a lipid bilayer.
Taku K1, Sasaki H, Kimura S, Imanishi Y. Biophys Chem. 1992 Oct;44(3):187-98.
Two types of chromophoric amphiphiles were synthesized: one of them possesses a molecular structure of N,N-dialkyl aromatic amino acid (5X18 type, where X is A or Cz), and the other alpha,gamma-dialkylglutamate connected to aromatic amino acid (mXG12 type, where m is an integer). 5-N-Ethylcarbazolyl and 9-anthryl groups were chosen as the chromophore, and introduced to each amino acid derivative. All the amphiphiles formed assembly showing gel-liquid crystalline phase transition. The phase-transition temperature of the assembly composed of mXG12-type amphiphile was higher than that of 5X18-type amphiphile. Absorption and CD spectra of 6-(trimethylammonium)hexanoyl-L-3-(5-N-ethylcarbazolyl) alanine N,N-dioctadecylamide bromide (5Cz18) in the assembly indicated the absence of strong ground-state interactions between the carbazolyl groups, while those of 6-(trimethylammonium)hexanoyl-L-3-(5-N-ethylcarbazolyl)alanyl-L-gl utamic acid alpha,gamma-didodecyl ester (5CzG12) or 11-(trimethylammonium)undecanoyl-L-3-(5-N-ethylcarbazolyl)al anyl-L-glutamic acid alpha,gamma-didodecyl ester (10CzG12) indicated the ground-state interactions based on dimer or higher aggregates.
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