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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 |
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Product Introduction
Ac-Nle-Pro-Nle-Asp-AMC is a synthetic peptide substrate that contains the fluorophore 7-amino-4-methylcoumarin (AMC), which is widely used in protease activity assays. This compound features a sequence that includes norleucine (Nle) and aspartic acid (Asp), which are linked to AMC, allowing for the detection of enzymatic cleavage through fluorescence emission. Upon cleavage by specific proteases, AMC is released, exhibiting a characteristic fluorescence that can be monitored to study enzyme kinetics and inhibitor screening in various biochemical research settings.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| 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 |
| 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) |
Product Specification
| Excitation | 340-360 nm |
| Emission | 440-460 nm |
| Storage | Store at -20°C |
Application
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.
Computed Properties
| 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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