Boc-Glu-Lys-Lys-AMC incorporates acidic and basic residues in a protected peptide attached to a fluorescent reporter. Its design supports investigation of protease recognition and substrate selectivity. Researchers examine its conformational and kinetic behavior. Applications include fluorescence-based assays, substrate optimization, and mechanistic evaluation.
CAT No: R2533
CAS No:73554-85-5
Synonyms/Alias:Boc-Glu-Lys-Lys-AMC;73554-85-5;BOC-GLU-LYS-LYS-MCA;Boc-Glu-Lys-Lys-Amc acetate salt;(4S)-5-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;SCHEMBL3258147;HY-P4319;DA-61807;FB110484;CS-0653500;(S)-5-(((S)-6-amino-1-(((S)-6-amino-1-((4-methyl-2-oxo-2H-chromen-7-yl)amino)-1-oxohexan-2-yl)amino)-1-oxohexan-2-yl)amino)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid;
Boc-Glu-Lys-Lys-AMC, also known as N-tert-Butoxycarbonyl-glutamyl-lysyl-lysine-7-amido-4-methylcoumarin, is a synthetic peptide substrate widely recognized for its utility in biochemical and enzymatic research. Featuring a protected N-terminal Boc group and a C-terminal 7-amido-4-methylcoumarin (AMC) fluorophore, this compound offers a unique combination of structural specificity and sensitive detection capabilities. The peptide sequence, incorporating glutamic acid and two lysine residues, is designed to mimic natural substrates of specific proteases, enabling precise monitoring of enzymatic cleavage events. The attached AMC moiety serves as a fluorogenic reporter, releasing a highly fluorescent signal upon enzymatic hydrolysis, which facilitates real-time quantification and kinetic studies. With its well-defined structure and versatile detection properties, Boc-Glu-Lys-Lys-AMC is an indispensable tool for researchers investigating proteolytic activity, enzyme specificity, and related biochemical processes.
Protease Activity Assays: Boc-Glu-Lys-Lys-AMC is extensively utilized in the development and optimization of protease activity assays, particularly for enzymes that recognize and cleave peptide bonds at lysine or glutamic acid residues. In these assays, the substrate is incubated with the protease of interest, and the enzymatic cleavage liberates the AMC group, resulting in a measurable fluorescent signal. This fluorescence can be continuously monitored using spectrophotometric or fluorometric instruments, providing quantitative data on enzyme kinetics, substrate specificity, and inhibitor efficacy. The high sensitivity and selectivity of this substrate make it ideal for screening protease inhibitors and characterizing novel proteolytic enzymes in a variety of research settings.
Enzyme Kinetics Studies: Researchers employ the AMC-labeled peptide in detailed enzyme kinetics studies to elucidate catalytic mechanisms and determine key parameters such as Km and Vmax. By varying substrate concentrations and monitoring the rate of AMC release, scientists can generate Michaelis-Menten plots and perform in-depth analyses of enzyme efficiency and substrate affinity. These insights are critical for understanding enzyme function at the molecular level and for designing more effective enzyme modulators or therapeutic candidates.
High-Throughput Screening: The fluorogenic nature of Boc-Glu-Lys-Lys-AMC makes it highly suitable for high-throughput screening (HTS) applications in drug discovery and biochemical research. Automated platforms can rapidly process hundreds or thousands of samples in microplate formats, using the substrate to identify compounds that modulate protease activity. The robust fluorescence signal and low background interference enable reliable detection of hits, accelerating the identification of lead molecules for further development.
Substrate Specificity Profiling: Scientists leverage this peptide substrate to probe the substrate specificity of various proteases, including serine, cysteine, and metalloproteases. By comparing cleavage rates across a panel of related substrates, researchers can map the preferences of different enzymes for specific amino acid sequences and structural motifs. This information is invaluable for designing selective substrates and inhibitors, as well as for understanding the physiological roles of proteases in complex biological systems.
Biochemical Pathway Elucidation: Boc-Glu-Lys-Lys-AMC plays a pivotal role in dissecting proteolytic pathways within cells and tissues. By tracking the generation of the fluorescent AMC product in the presence of cellular extracts or recombinant enzymes, investigators can identify active proteases, monitor pathway dynamics, and assess the impact of genetic or pharmacological interventions. These studies contribute to a deeper understanding of protease-regulated signaling networks and their implications for cellular function and disease processes.
In summary, the versatile applications of Boc-Glu-Lys-Lys-AMC span protease activity assays, enzyme kinetics, high-throughput screening, substrate specificity profiling, and biochemical pathway elucidation. Its unique combination of sequence specificity and fluorogenic detection empowers researchers to explore enzymatic processes with precision and efficiency, driving advances in biochemistry, molecular biology, and drug discovery. As a result, this substrate continues to be an essential resource for laboratories seeking to unravel the complexities of protease function and regulation.
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