H-β-(7-Methoxycoumarin-4-yl)-Ala-OH
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H-β-(7-Methoxycoumarin-4-yl)-Ala-OH

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H-β-(7-Methoxycoumarin-4-yl)-Ala-OH, a coumarin (O-methylumbelliferon) derivative for protein tagging, is used as a building block.

Category
L-Amino Acids
Catalog number
BAT-014410
CAS number
208660-68-8
Molecular Formula
C13H13NO5
Molecular Weight
263.25
IUPAC Name
(2S)-2-amino-3-(7-methoxy-2-oxochromen-4-yl)propanoic acid
Synonyms
(S)-2-Amino-3-(7-methoxycoumarin-4-yl)-propionic acid; 2H-1-Benzopyran-4-propanoic acid, α-amino-7-methoxy-2-oxo-, (αS)-; 3-(7-Methoxy-2-oxo-2H-chromen-4-yl)-L-alanine
Related CAS
133083-29-1 (rac-isomer)
Appearance
Pink Powder
Purity
≥95%
Density
1.372±0.06 g/cm3 (Predicted)
Boiling Point
508.6±50.0°C (Predicted)
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C13H13NO5/c1-18-8-2-3-9-7(4-10(14)13(16)17)5-12(15)19-11(9)6-8/h2-3,5-6,10H,4,14H2,1H3,(H,16,17)/t10-/m0/s1
InChI Key
IOHUIWNMQPWOAX-JTQLQIEISA-N
Canonical SMILES
COC1=CC2=C(C=C1)C(=CC(=O)O2)CC(C(=O)O)N

H-β-(7-Methoxycoumarin-4-yl)-Ala-OH, a fluorescent amino acid derivative, finds diverse applications in biochemistry and molecular biology. Here are the key applications presented with a high degree of perplexity and burstiness:

Fluorescent Labeling: Serving as a fluorescent probe, H-β-(7-Methoxycoumarin-4-yl)-Ala-OH is utilized for labeling peptides and proteins. Its remarkable fluorescence properties enable effortless detection and quantification in various analytical techniques like fluorescence microscopy and flow cytometry, proving invaluable in the exploration of protein localization, interactions, and dynamics within cellular environments.

Protease Activity Assays: This compound acts as a substrate in protease activity assays, enabling the monitoring of enzyme function. Upon cleavage by specific proteases, the fluorescence of H-β-(7-Methoxycoumarin-4-yl)-Ala-OH undergoes changes, providing a measurable signal indicative of enzymatic activity. Such assays play a vital role in studying protease kinetics, inhibitor screening, and unraveling the roles of proteases in intricate biological processes.

Fluorescence Resonance Energy Transfer (FRET) Studies: In FRET-based experiments, H-β-(7-Methoxycoumarin-4-yl)-Ala-OH is employed to study molecular interactions. When incorporated into donor-acceptor pairs, it facilitates the determination of distances and conformational changes between interacting molecules. This technique is essential for delving into protein-protein interactions, conformational alterations, and cellular signaling pathways, shedding light on intricate biological processes.

Drug Design and Development: Within pharmaceutical research, H-β-(7-Methoxycoumarin-4-yl)-Ala-OH plays a crucial role in the design and development of fluorescence-based bioassays. Its integration into potential drug candidates allows researchers to monitor and visualize compound localization, binding activity, and overall efficacy. This facilitates high-throughput screening of novel therapeutic agents, optimizing them for clinical use through comprehensive assessments.

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