Z-RLRGG-AMC is a fluorogenic substrate for the deubiquitinating enzyme isopeptidase T (IPaseT) and other ubiquitin C-terminal hydrolases (UCHs) based on the C-termini of ubiquitin with a kcat/Km value of 95 M⁻¹s⁻¹. Together with our product I-1685 it is used in continuous assays for precise mechanistic studies or microtiter plate assays for high-throughput inhibitor screening.
CAT No: R1912
CAS No:167698-69-3
Synonyms/Alias:167698-69-3;Z-Arg-Leu-Arg-Gly-Gly-AMC acetate salt;Cbz-Arg-Leu-Arg-Gly-Gly-AMC;DA-68806;
Chemical Name:benzyl N-[(2S)-5-(diaminomethylideneamino)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[[2-[[2-[(4-methyl-2-oxochromen-7-yl)amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate
Z-Arg-Leu-Arg-Gly-Gly-AMC is a synthetic peptide substrate widely utilized in biochemical and enzymological research. Structurally, it consists of a protected pentapeptide sequence conjugated to 7-amino-4-methylcoumarin (AMC), a fluorogenic leaving group. The design of this compound allows for precise monitoring of protease activity, as enzymatic cleavage releases the AMC moiety, resulting in a quantifiable fluorescence signal. Its specificity and sensitivity make it a valuable tool for investigating the functional properties of proteolytic enzymes, particularly those with preference for arginine- or leucine-containing motifs. The robust fluorescence response and well-characterized cleavage pattern position Z-Arg-Leu-Arg-Gly-Gly-AMC as an essential reagent in peptide-based assays and mechanistic studies.
Protease activity assays: One of the principal applications of this fluorogenic peptide is in the quantitative assessment of protease activity. Upon enzymatic hydrolysis at the designated peptide bond, the AMC group is liberated, producing a measurable fluorescent signal proportional to enzyme activity. This makes the substrate ideal for kinetic studies, inhibitor screening, and enzyme characterization in both basic and applied research settings. The sensitivity of the AMC readout enables detection of low-abundance protease activity, supporting studies in areas such as cell signaling, apoptosis, and protein degradation pathways.
Enzyme specificity profiling: The defined amino acid sequence of Z-Arg-Leu-Arg-Gly-Gly-AMC serves as a model substrate for determining substrate specificity of serine, cysteine, or other classes of proteases. Researchers can use this compound to delineate the cleavage preferences of novel or engineered enzymes, facilitating the mapping of substrate recognition motifs. This approach is instrumental in elucidating enzyme-substrate interactions, guiding protein engineering efforts, and informing the development of selective protease inhibitors.
High-throughput screening: The robust and reproducible fluorescence response of the AMC group upon peptide cleavage makes this substrate highly amenable to automated high-throughput screening (HTS) platforms. In pharmaceutical and biotechnology laboratories, it is frequently employed in large-scale screening assays to identify modulators of protease activity. The compatibility with microplate readers and automation technologies allows for rapid, parallel analysis of extensive compound libraries, accelerating the discovery of new enzyme inhibitors or activators.
Mechanistic enzymology: Z-Arg-Leu-Arg-Gly-Gly-AMC is extensively used in mechanistic studies to dissect the catalytic properties of proteolytic enzymes. By monitoring reaction rates under varying substrate concentrations, pH, or in the presence of cofactors, researchers can extract detailed kinetic parameters such as Km, Vmax, and inhibition constants. These data underpin mechanistic models of enzyme function and inform the rational design of more selective or potent enzyme modulators.
Peptide substrate validation: The compound is also valuable in validating the design of novel peptide substrates for protease assays. By serving as a reference standard, it allows for comparison of cleavage efficiency, fluorescence intensity, and background signal across different peptide constructs. This benchmarking process is critical in optimizing assay conditions, improving signal-to-noise ratios, and ensuring reliable interpretation of experimental results in both academic and industrial laboratories.
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