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 peptide substrate commonly used in biochemical research for the investigation of proteolytic enzymes, particularly those with trypsin-like specificity. Structurally, it features a carbobenzoxy-protected diarginine sequence conjugated to a 4-methoxy-β-naphthylamide group, making it a valuable tool for monitoring enzymatic cleavage events. The presence of the naphthylamide moiety allows for sensitive detection of substrate hydrolysis, which is central to a variety of enzymatic assays. Its defined peptide sequence and chromogenic properties support its widespread application in enzymology, molecular biology, and protein chemistry studies.
Enzyme Activity Assays: As a chromogenic peptide substrate, NA-Cbz-arg-arg 4-methoxy-B-naphthylamide is extensively employed to quantify the activity of serine proteases, especially those that recognize and cleave after arginine residues. Upon enzymatic cleavage, the release of the 4-methoxy-β-naphthylamine group can be monitored spectrophotometrically or fluorometrically, providing a reliable and sensitive readout of protease function. This makes the compound especially valuable in high-throughput screening and kinetic studies of enzyme inhibitors or activators.
Protease Specificity Profiling: The defined diarginine motif within the substrate enables researchers to dissect the substrate specificity of various proteolytic enzymes. By comparing the rate and efficiency of cleavage with other peptide substrates, scientists can elucidate the substrate preferences and catalytic mechanisms of target proteases. Such profiling is essential for understanding enzyme function, mapping active sites, and guiding the design of selective inhibitors for research purposes.
Biochemical Pathway Elucidation: In studies of complex biological samples, NA-Cbz-arg-arg 4-methoxy-B-naphthylamide serves as a probe to identify and characterize proteolytic activities present in tissue extracts, cell lysates, or purified protein mixtures. Its use facilitates the discovery of novel proteases or the monitoring of proteolytic processing events within signaling pathways. This application supports investigations into regulatory mechanisms governing protein turnover and post-translational modifications.
Quality Control in Enzyme Production: In industrial and research settings where proteases are produced or purified, this peptide substrate is utilized as part of quality assurance protocols. Its rapid and quantifiable response to enzymatic cleavage enables consistent assessment of protease potency, stability, and lot-to-lot variability. Such quality control measures are critical for ensuring reproducibility and reliability in downstream applications involving proteolytic enzymes.
Inhibitor Screening and Drug Discovery: The substrate's well-characterized cleavage profile makes it an excellent choice for screening chemical libraries or biological extracts for compounds that modulate protease activity. By incorporating it into assay platforms, researchers can efficiently identify and characterize potential protease inhibitors, which are of significant interest in the study of enzyme regulation and the development of research tools targeting proteolytic pathways. This application underpins advancements in fundamental enzymology and chemical biology research.
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