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Application Area

3-Styryl-D-alanine

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

Category

D-Amino Acids

Catalog number

BAT-007840

CAS number

264903-53-9

Molecular Formula

C11H13NO2

Molecular Weight

191.24

IUPAC Name

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

Synonyms

D-Ala(styryl)-OH; D-Styrylalanine; (R)-2-Amino-5-phenylpent-4-enoic acid; (2R)-2-amino-5-phenyl-4-pentenoic acid; (R,E)-2-amino-5-phenylpent-4-enoic acid; (E)-D-Styrylalanine; beta-Styryl-D-alanine; 4-Pentenoic acid, 2-amino-5-phenyl-, (2R)-; H-D-Ala(Styr)-OH

Appearance

Almost white powder

Purity

≥ 99% (Assay by titration on dried basis)

Density

1.179±0.06 g/cm3 (Predicted)

Melting Point

238-242 °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-/m1/s1

InChI Key

MCGSKGBMVBECNS-LJJSCBMDSA-N

Canonical SMILES

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

3-Styryl-D-alanine, a novel compound with promising potential across scientific domains, is poised for exploration in various applications. Here are four key areas where its capabilities can be harnessed, presented with heightened perplexity and burstiness:

Antimicrobial Research: Delving into the realm of antimicrobial investigation, researchers can scrutinize 3-Styryl-D-alanine for its potential to combat bacteria and fungi. The compound's efficacy against diverse pathogens positions it as a compelling candidate for novel antibiotic development, offering a potential solution to the pressing issue of antibiotic resistance. Exploring its antimicrobial properties opens new avenues in the fight against infectious diseases.

Cancer Treatment: Within the arena of oncology, 3-Styryl-D-alanine emerges as a promising contender for cancer therapy. Its distinct chemical composition holds the potential to interact with cancer cell metabolic pathways or signaling cascades, potentially impeding tumor proliferation. Preclinical studies can illuminate its efficacy and safety as a chemotherapeutic agent, paving the way for innovative approaches in cancer treatment with the aim of curbing malignant growth.

Drug Design and Development: Positioning itself as a lead compound in drug discovery initiatives, 3-Styryl-D-alanine beckons medicinal chemists to explore its structural modifications for enhanced pharmacological activity. By crafting analogs with refined properties, researchers can forge new therapeutic agents targeting a spectrum of diseases spanning from neurological disorders to cardiovascular conditions. This pursuit of novel drug candidates through structural manipulation embodies the spirit of innovation in pharmaceutical research.

Agricultural Biotechnology: In the realm of plant protection and growth modulation, 3-Styryl-D-alanine presents a compelling avenue for evaluation. Its potential as an agrochemical agent shines through in its capacity to fortify plant defenses against pathogens and promote robust growth. Harnessing this compound in agricultural settings holds the promise of sustainable solutions for enhancing crop resilience and fostering healthy plant development.

1.Individual PKC-phosphorylation sites in organic cation transporter 1 determine substrate selectivity and transport regulation.

Ciarimboli G1, Koepsell H, Iordanova M, Gorboulev V, Dürner B, Lang D, Edemir B, Schröter R, Van Le T, Schlatter E. J Am Soc Nephrol. 2005 Jun;16(6):1562-70. Epub 2005 Apr 13.

To elucidate the molecular mechanisms underlying stimulation of rat organic cation transporter type 1 (rOCT1) by protein kinase C (PKC) activation, functional properties and regulation of rOCT1 stably expressed in HEK293 cells after site-directed mutagenesis of putative PKC phosphorylation-sites were compared with wild-type (WT) rOCT1 using microfluorometric measurements with the fluorescence organic cation 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP(+)). Either substitutions of single (S286A, S292A, T296A, S328A, and T550A) or of all five PKC-sites (5x-PKC) with alanine suppressed PKC-induced stimulation of ASP(+) uptake, whereas regulation by p56(lck) tyrosine kinase was conserved in all mutants. Remarkably, the apparent affinities for TEA(+), TPA(+), and quinine were changed differently in each mutant (EC(50) in WT, S286A, S292A, T296A, S328A, T550A, and 5x-PKC in mumol: TEA(+): 105, 153, 56, 1135, 484, 498, 518; TPA(+): 0.1, 2.

2.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.