NA-Cbz-arg-arg 4-methoxy-β-naphthylamide is a fluorogenic dipeptide containing a methoxy-naphthylamide reporter for monitoring proteolysis. The arginine-rich sequence enhances binding to protease active sites. Researchers use it in kinetic assays and inhibitor characterization. Cbz protection stabilizes the substrate and modulates synthetic reactivity.
CAT No: R2275
CAS No:100900-19-4
Synonyms/Alias:100900-19-4;NA-CBZ-ARG-ARG 4-METHOXY-B-NAPHTHYLAMIDE;Acetic acid;benzyl N-[(2S)-5-(diaminomethylideneamino)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methoxynaphthalen-2-yl)amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate;Na-cbz-arg-arg 4-methoxy-b-naphthylamideacetate;Z-RR-MNA;DTXSID50746704;N-alpha-CBZ-L-arginyl-L-arginine 4-methoxy-beta-naphthylamide, acetate salt;DA-55964;G92094;Z-Arg-Arg 4-methoxy-beta-naphthylamide acetate salt;Acetic acid--N~2~-[(benzyloxy)carbonyl]-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-N-(4-methoxynaphthalen-2-yl)-L-ornithinamide (1/1);Benzyl ((S)-5-guanidino-1-(((S)-5-guanidino-1-((4-methoxynaphthalen-2-yl)amino)-1-oxopentan-2-yl)amino)-1-oxopentan-2-yl)carbamate acetate;
NA-Cbz-arg-arg 4-methoxy-B-naphthylamide is a synthetic dipeptidyl substrate known for its utility in enzymatic studies, particularly those focusing on protease activity. This compound features a carbobenzoxy-protected arginine-arginine sequence conjugated to a 4-methoxy-β-naphthylamide group, which serves as a chromogenic or fluorogenic leaving group during enzymatic cleavage. Its unique structure allows for sensitive detection of enzymatic reactions, making it a valuable tool in biochemical research. Researchers often select this compound for its stability under experimental conditions and its ability to yield clear, quantifiable results in a range of assay formats. The presence of the naphthylamide moiety enables straightforward spectroscopic monitoring, facilitating real-time analysis of proteolytic processes. As a result, NA-Cbz-arg-arg 4-methoxy-B-naphthylamide has gained recognition in the scientific community as a reliable substrate for investigating enzyme specificity, kinetics, and inhibition.
Enzyme Activity Assays: NA-Cbz-arg-arg 4-methoxy-B-naphthylamide is widely applied in the development and optimization of enzyme activity assays, particularly those involving serine and cysteine proteases. By incorporating this substrate into in vitro assay systems, researchers can monitor proteolytic cleavage through the release of the 4-methoxy-β-naphthylamide group, which generates a measurable fluorescent or colorimetric signal. This approach enables the quantification of enzymatic activity, assessment of substrate specificity, and comparison of protease efficiency under various experimental conditions. The high sensitivity of the detection method supports detailed kinetic analyses, facilitating the elucidation of enzyme mechanisms and the effects of potential inhibitors or activators.
Protease Inhibitor Screening: In the search for novel protease inhibitors, NA-Cbz-arg-arg 4-methoxy-B-naphthylamide serves as an essential screening substrate. Its well-defined peptide sequence and chromogenic leaving group allow for rapid identification of compounds that modulate protease activity. By incorporating it into high-throughput screening platforms, researchers can efficiently evaluate large libraries of chemical entities for inhibitory effects, supporting the discovery of new molecular probes or lead compounds for further development. The substrate's compatibility with automated assay systems ensures reproducible and scalable results, streamlining the inhibitor discovery process.
Substrate Specificity Profiling: The use of NA-Cbz-arg-arg 4-methoxy-B-naphthylamide extends to the profiling of protease substrate preferences. By comparing the cleavage rates of this compound with those of structurally related substrates, scientists can gain insights into the amino acid recognition motifs favored by specific enzymes. This information is crucial for understanding protease function in biological systems and for designing selective substrates or inhibitors. The straightforward spectroscopic detection of product formation allows for precise and comparative analyses, contributing to the mapping of enzyme-substrate interactions.
Biochemical Pathway Elucidation: Researchers utilize NA-Cbz-arg-arg 4-methoxy-B-naphthylamide to explore proteolytic events within complex biochemical pathways. By introducing the substrate into cell lysates or reconstituted systems, it becomes possible to monitor the activity of endogenous or recombinant proteases in real time. This application aids in the identification of active proteolytic components, the characterization of their roles in regulatory cascades, and the investigation of post-translational modification processes. The quantitative nature of the assay readouts supports robust pathway analysis and hypothesis testing.
Quality Control in Enzyme Production: In the context of enzyme manufacturing and purification, NA-Cbz-arg-arg 4-methoxy-B-naphthylamide is employed as a quality control reagent to assess protease activity in production batches. By measuring the substrate turnover rate, manufacturers can verify enzyme potency, monitor batch-to-batch consistency, and detect potential contaminants or degradation products. The substrate's reliability and ease of use make it an indispensable tool for ensuring the functionality of enzyme preparations destined for research or industrial applications. This quality assurance step is vital for maintaining the integrity of downstream experimental workflows and for supporting the reproducibility of scientific results.
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