Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin is a fluorogenic peptide substrate incorporating a coumarin reporter for sensitive protease monitoring. The tripeptide core enhances recognition of arginine-specific catalytic sites. Researchers use it in kinetic assays, inhibitor studies, and structural-functional mapping. Its Boc protection improves synthetic robustness.
CAT No: R2303
CAS No:113866-20-9
Synonyms/Alias:Boc-Gln-Ala-Arg-Mca;Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin;Boc-Gln-Ala-Arg-AMC;113866-20-9;Boc-Gln-Ala-Arg-7-amido-4-methylcoumarin;tert-butyl N-[(2S)-5-amino-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamate;Boc-Gln-Ala-Arg-AMCA;SCHEMBL2143298;CHEBI:84832;Boc-Gln-Ala-Arg-methylcoumarin amide;Boc-Gln-Ala-Arg-4-methylcoumaryl-7-amide;Boc-Gln-Ala-Arg-4-methyl-coumaryl-7-amide;Q27158101;N(2)-(tert-butoxycarbonyl)-L-glutaminyl-L-alanyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-argininamide;N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutaminyl-L-alanyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-argininamide;tert-butyl (S)-5-amino-1-((S)-1-((S)-5-guanidino-1-(4-methyl-2-oxo-2H-chromen-7-ylamino)-1-oxopentan-2-ylamino)-1-oxopropan-2-ylamino)-1,5-dioxopentan-2-ylcarbamate;
Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin is a synthetic peptide substrate widely utilized in enzymology and biochemical research, particularly for the investigation of protease activity. Structurally, it consists of a tripeptide sequence—glutamine, alanine, and arginine—protected at the N-terminus with a tert-butyloxycarbonyl (Boc) group, and conjugated at the C-terminus to the fluorogenic moiety 7-amino-4-methylcoumarin (AMC). This design enables the substrate to serve as a sensitive reporter in assays where proteolytic cleavage liberates the fluorescent AMC, providing a direct readout of enzyme function. Its flexibility and specificity make it a valuable tool for characterizing proteolytic enzymes, optimizing assay conditions, and supporting high-throughput screening in drug discovery and biochemical analysis.
Protease Activity Assays: As a fluorogenic peptide substrate, Boc-Gln-Ala-Arg-AMC is extensively used to quantify the activity of serine and cysteine proteases, including trypsin-like and thrombin-like enzymes. Upon enzymatic cleavage at the arginine residue, the AMC group is released, generating a measurable fluorescent signal. This real-time detection capability is essential for kinetic studies, enabling accurate determination of enzyme specificity, catalytic efficiency, and inhibitor potency. Its application is particularly significant in profiling protease selectivity and dissecting substrate preferences in complex biological mixtures.
Enzyme Inhibitor Screening: The substrate's robust signal generation and compatibility with microplate formats make it ideal for high-throughput screening of protease inhibitors. Researchers leverage the sensitivity of AMC fluorescence to assess the inhibitory effects of candidate compounds on target enzymes. By monitoring changes in fluorescence intensity, it becomes possible to rapidly identify and characterize inhibitors, supporting early-stage drug discovery and the development of novel modulators of proteolytic pathways. The substrate's defined sequence ensures reproducibility and facilitates comparative analyses across different inhibitor classes.
Biochemical Pathway Elucidation: In studies of cellular and molecular biology, this peptide-AMC conjugate serves as a probe to dissect protease function within broader signaling cascades. By introducing the substrate into cell lysates or reconstituted systems, researchers can monitor endogenous enzyme activities and map proteolytic events underlying physiological or pathological processes. The fluorogenic readout provides temporal resolution, enabling the investigation of dynamic changes in enzyme activity in response to stimuli, genetic modifications, or environmental factors.
Assay Development and Optimization: The well-characterized cleavage properties and stable fluorescence of the AMC moiety support the development and refinement of quantitative protease assays. Scientists employ Boc-Gln-Ala-Arg-AMC to validate assay performance parameters such as sensitivity, linearity, and dynamic range. Its use is instrumental in calibrating instrumentation, optimizing buffer conditions, and establishing assay protocols for both routine laboratory analysis and advanced research applications. The substrate's versatility facilitates adaptation to a variety of detection platforms, including fluorescence plate readers and automated systems.
Analytical Method Validation: Beyond routine enzyme assays, the substrate is valuable in validating analytical methods for protease quantification in complex biological samples. Its defined structure and predictable cleavage behavior allow for the assessment of assay robustness, reproducibility, and interference from sample matrices. This supports quality control in research and industrial settings, where accurate measurement of protease activity is critical for product development, process monitoring, and compliance with research protocols. The use of such peptide-based fluorogenic substrates ensures methodological consistency and enhances the reliability of biochemical analyses.
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