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Application Area

3-Styryl-L-alanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

L-Amino Acids

Catalog number

BAT-007841

CAS number

267650-37-3

Molecular Formula

C11H13NO2

Molecular Weight

191.24

IUPAC Name

(E,2S)-2-amino-5-phenylpent-4-enoic acid

Synonyms

L-Ala(styryl)-OH; (S)-3-(amino)-5-phenyl-4-pentenoic acid dicyclohexylamine salt; L-Styrylalanine; (S)-2-Amino-5-phenylpent-4-enoic acid; (2S,4E)-2-amino-5-phenylpent-4-enoic acid; L-Styryl alanine; H-Ala(Styr)-OH; (E)-L-Styrylalanine; beta-Styryl-L-alanine; (S,E)-2-amino-5-phenylpent-4-enoic acid

Appearance

White to off-white powder

Purity

≥ 99% (HPLC)

Density

1.179±0.06 g/cm3 (Predicted)

Melting Point

132-138 °C

Boiling Point

399.4±42.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C11H13NO2/c12-10(11(13)14)8-4-7-9-5-2-1-3-6-9/h1-7,10H,8,12H2,(H,13,14)/b7-4+/t10-/m0/s1

InChI Key

MCGSKGBMVBECNS-QBBOHKLWSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CCC(C(=O)O)N

Organic compound 3-Styryl-L-alanine finds extensive applications in biomedical and pharmaceutical fields. Here are the key applications explored with high perplexity and burstiness:

Cancer Research: Delving into the realm of cancer research, scientists investigate the potential anticancer properties of 3-Styryl-L-alanine. By analyzing its impact on cancer cell proliferation, apoptosis, and metastasis, researchers aim to unveil novel therapeutic avenues. The unique structural framework of this compound serves as a cornerstone for the creation of innovative chemotherapeutic agents, driving forward the fight against cancer.

Drug Development: Positioned at the forefront of drug development, 3-Styryl-L-alanine, an amino acid derivative, plays a pivotal role in shaping the design of next-generation pharmaceuticals. Through the strategic modification of its structural elements, scientists enhance drug activity and specificity, ushering in a new era of precision medicine. This compound's exceptional molecular scaffold acts as a cornerstone for synthesizing therapeutic agents targeting a myriad of medical conditions, propelling pharmaceutical innovation.

Biomarker Discovery: Within the realm of biomedical exploration, 3-Styryl-L-alanine emerges as a promising candidate for biomarker discovery in disease diagnostics. By probing its presence and concentration in biological samples, researchers strive to unveil early indicators of pathological conditions, paving the way for timely intervention and disease monitoring. This application stands as a critical tool in the arsenal of early disease detection.

Enzymatic Studies: In the domain of enzymatic research, 3-Styryl-L-alanine serves as a valuable probe for unraveling enzyme-substrate interactions and catalytic mechanisms. Researchers leverage this compound to dissect the intricacies of specific enzymes participating in metabolic pathways, shedding light on fundamental biochemical processes. This knowledge fuels the advancement of enzyme function understanding and informs the development of enzyme inhibitors as potential therapeutic modalities.

1.An N-terminal threonine mutation produces an efflux-favorable, sodium-primed conformation of the human dopamine transporter.

Fraser R1, Chen Y1, Guptaroy B1, Luderman KD1, Stokes SL1, Beg A1, DeFelice LJ1, Gnegy ME2. Mol Pharmacol. 2014 Jul;86(1):76-85. doi: 10.1124/mol.114.091926. Epub 2014 Apr 21.

The dopamine transporter (DAT) reversibly transports dopamine (DA) through a series of conformational transitions. Alanine (T62A) or aspartate (T62D) mutagenesis of Thr62 revealed T62D-human (h)DAT partitions in a predominately efflux-preferring conformation. Compared with wild-type (WT), T62D-hDAT exhibits reduced [(3)H]DA uptake and enhanced baseline DA efflux, whereas T62A-hDAT and WT-hDAT function in an influx-preferring conformation. We now interrogate the basis of the mutants' altered function with respect to membrane conductance and Na(+) sensitivity. The hDAT constructs were expressed in Xenopus oocytes to investigate if heightened membrane potential would explain the efflux characteristics of T62D-hDAT. In the absence of substrate, all constructs displayed identical resting membrane potentials. Substrate-induced inward currents were present in oocytes expressing WT- and T62A-hDAT but not T62D-hDAT, suggesting equal bidirectional ion flow through T62D-hDAT.

2.Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds.

Ton TM1, Himawan F, Chang JW, Chan PW. Chemistry. 2012 Sep 17;18(38):12020-7. doi: 10.1002/chem.201201219. Epub 2012 Aug 13.

A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)(2)+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO(2) Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine.