L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt
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L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt

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Category
Other Unnatural Amino Acids
Catalog number
BAT-007995
CAS number
96594-10-4
Molecular Formula
C13H14N2O3 C2HF3O2
Molecular Weight
360.29
L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt
IUPAC Name
(2S)-2-amino-N-(4-methyl-2-oxochromen-7-yl)propanamide;2,2,2-trifluoroacetic acid
Synonyms
L-Alanine-AMC TFA salt; (2S)-2-Amino-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-propanamide 2,2,2-trifluoroacetate
Related CAS
77471-41-1 (free base)
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Melting Point
199-205 °C
Boiling Point
490.1°C at 760mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H14N2O3.C2HF3O2/c1-7-5-12(16)18-11-6-9(3-4-10(7)11)15-13(17)8(2)14;3-2(4,5)1(6)7/h3-6,8H,14H2,1-2H3,(H,15,17);(H,6,7)/t8-;/m0./s1
InChI Key
YYGKKBUKGNFDJW-QRPNPIFTSA-N
Canonical SMILES
CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(C)N.C(=O)(C(F)(F)F)O

L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt, a synthetic compound widely employed in biochemical and molecular biology research, offers diverse applications. Here are the key applications, narrated with heightened perplexity and burstiness:

Fluorogenic Substrate for Enzyme Assays: This compound features prominently as a fluorogenic substrate in enzyme activity assays. When cleaved by specific enzymes like proteases or hydrolases, it liberates a fluorescent coumarin moiety. This ensuing fluorescence is measurable, facilitating the determination of enzyme activity kinetics and potential inhibitors, unraveling the intricate dance of biochemical reactions.

Protein Digestion Studies: Amidst investigations into protein structure and function, L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt emerges as a crucial substrate for exploring proteolytic activities. Researchers delve into how distinct proteases cleave specific peptide bonds, unraveling the mysteries of protein degradation pathways and identifying elusive protease inhibitors, transcending boundaries in unraveling the complexity of protein dynamics.

Drug Screening: Let's pivot to the realm of drug discovery, where this compound shines in high-throughput screening assays. By integrating it into assays, pharmaceutical visionaries can swiftly evaluate the inhibitory effects of various compounds on target enzymes. This streamlined approach expedites the discovery of novel drug candidates and therapeutic molecules, sparking transformative advancements in pharmacological innovation.

Cell-Based Assays: Embarking on cellular explorations, L-Alanine-7-amido-4-methylcoumarin trifluoroacetic acid salt takes center stage in monitoring intracellular enzyme activities. Its ability to infiltrate cells and interact with intracellular enzymes, culminating in illuminating fluorescence, offers real-time glimpses into the dynamic world of cellular enzyme regulation. This methodological innovation enriches studies in cell biology, transcending conventional boundaries in unraveling cellular mysteries.

1. Comprehensive overview of recent preparation and application trends of various open tubular capillary columns in separation science
Won Jo Cheong, Faiz Ali, Yune Sung Kim, Jin Wook Lee J Chromatogr A. 2013 Sep 20;1308:1-24. doi: 10.1016/j.chroma.2013.07.107. Epub 2013 Aug 5.
Open tubular (OT) capillary columns have been increasingly used in a variety of fields of separation science such as CEC, LC, and SPE. Especially their application in CEC has attracted a lot of attention for their outstanding separation performance. Various forms of OT stationary phase materials have been employed such as in-situ prepared polymers, molecular imprinted polymers (MIPs), brush ligands, host ligands, block copolymers, aptamers, carbon nanotubes, polysaccharides, proteins, tentacles, nanoparticles, monoliths, and polyelectrolyte multi-layers. They have been prepared either in the chemically bound format or physically adsorbed format. Sol-gel technologies and nanoparticles have been sometimes involved in their preparation. There have been also some unique miscellaneous studies, for example, adopting preferentially adsorbed mobile phase components as stationary phases. In this review, recent progresses since mostly 2007 will be critically discussed in detail with some summarized descriptions for the work before the date.
2. Antifungal Activity of Amphiphilic Perylene Bisimides
Vicky C Roa-Linares, Ana C Mesa-Arango, Ramón J Zaragozá, Miguel A González-Cardenete Molecules. 2022 Oct 14;27(20):6890. doi: 10.3390/molecules27206890.
Perylene-based compounds, either naturally occurring or synthetic, have shown interesting biological activities. In this study, we report on the broad-spectrum antifungal properties of two lead amphiphilic perylene bisimides, compounds 4 and 5, which were synthesized from perylene-3,4,9,10-tetracarboxylic dianhydride by condensation with spermine and an ammonium salt formation. The antifungal activity was evaluated using a collection of fungal strains and clinical isolates from patients with onychomycosis or sporotrichosis. Both molecules displayed an interesting antifungal profile with MIC values in the range of 2-25 μM, being as active as several reference drugs, even more potent in some particular strains. The ammonium trifluoroacetate salt 5 showed the highest activity with a MIC value of 2.1 μM for all tested Candida spp., two Cryptococcus spp., two Fusarium spp., and one Neoscytalidium spp. strain. Therefore, these amphiphilic molecules with the perylene moiety and cationic ammonium side chains represent important structural features for the development of novel antifungals.
3. Forced degradation and impurity profiling: recent trends in analytical perspectives
Deepti Jain, Pawan Kumar Basniwal J Pharm Biomed Anal. 2013 Dec;86:11-35. doi: 10.1016/j.jpba.2013.07.013. Epub 2013 Jul 31.
This review describes an epigrammatic impression of the recent trends in analytical perspectives of degradation and impurities profiling of pharmaceuticals including active pharmaceutical ingredient (API) as well as drug products during 2008-2012. These recent trends in forced degradation and impurity profiling were discussed on the head of year of publication; columns, matrix (API and dosage forms) and type of elution in chromatography (isocratic and gradient); therapeutic categories of the drug which were used for analysis. It focuses distinctly on comprehensive update of various analytical methods including hyphenated techniques for the identification and quantification of thresholds of impurities and degradants in different pharmaceutical matrices.
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