Tert-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin links protected peptide residues to a fluorescent reporter for monitoring proteolytic cleavage. The hydrophobic and acidic residues shape substrate recognition. Arginine promotes strong electrostatic interactions with catalytic sites. Applications include kinetic assays, fluorogenic substrate development, and mechanistic enzymology.
CAT No: R2672
CAS No:65147-06-0
Synonyms/Alias:tertiary-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin;Biggam;65147-06-0;(4S)-5-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[(4-methyl-2-oxochromen-7-yl)amino]pentanoyl]amino]-2-oxoethyl]amino]-4-[[(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-5-oxopentanoic acid;tertiary-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin;L-Argininamide, N-((1,1-dimethylethoxy)carbonyl)-L-isoleucyl-L-alpha-glutamylglycyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-;DTXSID90983717;4-[(2-{[tert-Butoxy(hydroxy)methylidene]amino}-1-hydroxy-3-methylpentylidene)amino]-5-hydroxy-5-[(2-hydroxy-2-{[N~2~-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)arginyl]imino}ethyl)imino]pentanoic acid;
Tertiary-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin, also known as Boc-Ile-Glu-Gly-Arg-AMC, is a synthetic peptide substrate widely employed in biochemical research and enzymology. Its structure features a protected peptide chain linked to the fluorogenic 7-amino-4-methylcoumarin (AMC) moiety, enabling sensitive detection of proteolytic activity. The presence of the Boc group ensures stability and ease of handling during experimental procedures, while the specific amino acid sequence provides selectivity for targeted enzymatic assays. This compound's versatility lies in its ability to release the highly fluorescent AMC upon enzymatic cleavage, making it a valuable tool for real-time monitoring of enzyme kinetics and substrate specificity. Researchers benefit from its robust performance in both in vitro and high-throughput screening environments, where precision and reproducibility are critical.
Protease Activity Assays: Boc-Ile-Glu-Gly-Arg-AMC is extensively utilized as a fluorogenic substrate in protease activity assays, particularly for enzymes that recognize and cleave after arginine residues. Upon enzymatic hydrolysis, the AMC group is liberated, producing a measurable fluorescent signal that can be quantitatively monitored using spectrofluorometric techniques. This enables researchers to determine enzyme activity, screen for potential inhibitors, and analyze substrate specificity under various experimental conditions. The compound's high sensitivity and low background fluorescence make it an ideal choice for kinetic studies and enzyme characterization.
Enzyme Kinetics Studies: In the field of enzyme kinetics, this peptide-AMC conjugate serves as a reliable tool for elucidating catalytic mechanisms and determining kinetic parameters such as Km and Vmax. By providing a continuous, real-time readout of enzymatic reactions, it allows for precise quantification of reaction rates and facilitates the comparison of different enzyme variants or conditions. Its use in Michaelis-Menten and inhibition studies supports the development of mechanistic models and aids in the rational design of enzyme modulators.
High-Throughput Screening: The fluorogenic properties of tertiary-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin make it particularly suitable for high-throughput screening (HTS) applications. Automated platforms can rapidly assess thousands of samples for protease activity or inhibition, accelerating the discovery of novel bioactive compounds. Its compatibility with multi-well plate formats and minimal interference with assay components ensure reproducibility and scalability in pharmaceutical and academic research settings.
Biochemical Pathway Analysis: Researchers employ Boc-Ile-Glu-Gly-Arg-AMC to dissect complex biochemical pathways involving proteolytic processing. By tracking the release of AMC, it is possible to monitor specific cleavage events within multi-enzyme cascades or cellular extracts. This facilitates the identification of regulatory checkpoints and the mapping of protease-substrate interactions, contributing to a deeper understanding of cellular regulation and signaling networks.
Substrate Specificity Profiling: The defined sequence and fluorogenic nature of this compound allow for detailed profiling of protease substrate preferences. By comparing its cleavage with that of other peptide-AMC conjugates, investigators can delineate the selectivity of individual enzymes or enzyme families. Such profiling is invaluable for developing targeted inhibitors, engineering enzyme specificity, and elucidating the physiological roles of proteolytic enzymes in various biological contexts.
Peptide-based Biosensor Development: The unique properties of tertiary-Butyloxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-7-amino-4-methylcoumarin have also been harnessed in the design of peptide-based biosensors. By integrating this substrate into sensor platforms, researchers can achieve real-time detection of protease activity in complex samples, such as cell lysates or environmental matrices. Its rapid and specific response to enzymatic cleavage supports applications in diagnostics, environmental monitoring, and basic research, where sensitive and selective detection of proteolytic events is required.
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