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Ac-Nle-Pro-Nle-Asp-AMC | CAS 355140-49-7
| Catalog Number | A18-0047 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C33H45N5O9 |
| Molecular Weight | 655.74 |
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| A18-0047 | -- | -- |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Ac-Nle-Pro-Nle-Asp-AMC is a substrate for proteasomes. It can be cleaved by the caspase-like site of proteasome, also known as postglutamyl peptide hydrolase (PGPH). AMC (7-amino-4-methylcoumarin) is released and produces the fluorescence utilized to quantify the caspase-like site activity. Ac-Nle-Pro-Nle-Asp-AMC also inhibits the chymotrypsin-like activity of the proteasome allosterically when bound to the caspase-like site.
Chemical Information
Product Specification
Application
Computed Properties
| Synonyms | Ac-Nle-Pro-Nle-Asp-7-amido-4-Methylcoumarin; Ac-nLPnLD-AMC; N-acetyl-L-norleucyl-L-prolyl-L-norleucyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-α-asparagine; L-α-Asparagine, N-acetyl-L-norleucyl-L-prolyl-L-norleucyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-; (3S)-4-Hydroxy-3-({(2S)-1-hydroxy-2-[(hydroxy{(2S)-1-[N-(1-hydroxyethylidene)-L-norleucyl]-2-pyrrolidinyl}methylene)amino]hexylidene}amino)-4-[(4-methyl-2-oxo-2H-chromen-7-yl)imino]butanoic acid |
| Purity | ≥98% |
| IUPAC Name | (3S)-3-[[(2S)-2-[[(2S)-1-[(2S)-2-acetamidohexanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]amino]-4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid |
| Canonical SMILES | CCCCC(C(=O)NC(CC(=O)O)C(=O)NC1=CC2=C(C=C1)C(=CC(=O)O2)C)NC(=O)C3CCCN3C(=O)C(CCCC)NC(=O)C |
| InChI | InChI=1S/C33H45N5O9/c1-5-7-10-23(36-32(45)26-12-9-15-38(26)33(46)24(11-8-6-2)34-20(4)39)30(43)37-25(18-28(40)41)31(44)35-21-13-14-22-19(3)16-29(42)47-27(22)17-21/h13-14,16-17,23-26H,5-12,15,18H2,1-4H3,(H,34,39)(H,35,44)(H,36,45)(H,37,43)(H,40,41)/t23-,24-,25-,26-/m0/s1 |
| InChIKey | WPTAROWBMZVECB-CQJMVLFOSA-N |
| Solubility | Soluble in Acetic Acid |
| Density | 1.278±0.06 g/cm3 (Predicted) |
| Appearance | White Lyophilized Powder |
| Boiling Point | 1028.3±65.0°C (Predicted) |
| Excitation | 340-360 nm |
| Emission | 440-460 nm |
| Storage | Store at -20°C |
Ac-Nle-Pro-Nle-Asp-AMC, a fluorogenic peptide substrate with diverse biochemical applications, is a pivotal tool in scientific research.
Protease Activity Assays: Widely utilized in biochemical studies, Ac-Nle-Pro-Nle-Asp-AMC serves as a valuable tool for assessing protease activity. Upon cleavage by a protease, it releases a fluorescent molecule, enabling easy detection. This method allows researchers to precisely measure enzyme activity and explore the effects of protease modulators in pharmaceutical and diagnostic contexts.
Biochemical Research: In the realm of enzyme-substrate interactions, Ac-Nle-Pro-Nle-Asp-AMC plays a crucial role in investigations of specificity and kinetics. Researchers leverage this substrate to unravel how different enzymes recognize and cleave peptide bonds. This data is instrumental in uncovering enzyme mechanisms and developing targeted drugs with enhanced efficacy.
High-Throughput Screening (HTS): Integral to HTS platforms, Ac-Nle-Pro-Nle-Asp-AMC aids in the identification of potential protease modulators. Its fluorogenic properties enable rapid and sensitive detection, making it ideal for screening vast compound libraries. This application expedites drug discovery processes and streamlines the search for novel therapeutic agents with promising clinical applications.
Cellular Imaging: In the realm of live-cell imaging, Ac-Nle-Pro-Nle-Asp-AMC facilitates the visualization of protease activity within cells. This substrate enters cells and emits fluorescence upon cleavage, offering real-time insights into intracellular enzyme dynamics. Such applications are important for studying dynamic biological processes and gaining a deeper understanding of disease pathology at the cellular level.
| XLogP3 | 2.3 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 16 |
| Exact Mass | 655.32172803 g/mol |
| Monoisotopic Mass | 655.32172803 g/mol |
| Topological Polar Surface Area | 200Ų |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Complexity | 1220 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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