Ac-Nle-Pro-Nle-Asp-AMC

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Ac-Nle-Pro-Nle-Asp-AMC

Ac-Nle-Pro-Nle-Asp-AMC | 355140-49-7

Catalog Number A18-0047
Category Fluorescent Enzyme Substrates
Molecular Formula C33H45N5O9
Molecular Weight 655.74
Catalog Number Size Price Quantity

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

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
InChI Key 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
  • Application
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.

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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