Fmoc-L-Aspartic acid α-7-amido-4-methylcoumarin
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Fmoc-L-Aspartic acid α-7-amido-4-methylcoumarin

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Category
Fmoc-Amino Acids
Catalog number
BAT-003737
CAS number
238084-15-6
Molecular Formula
C29H24N2O7
Molecular Weight
512.53
Fmoc-L-Aspartic acid α-7-amido-4-methylcoumarin
IUPAC Name
(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid
Synonyms
Fmoc-L-Asp-AMC; (3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid
Appearance
White amorphous powder
Purity
≥ 97% (HPLC)
Density
1.400±0.06 g/cm3
Boiling Point
824.9±65.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C29H24N2O7/c1-16-12-27(34)38-25-13-17(10-11-18(16)25)30-28(35)24(14-26(32)33)31-29(36)37-15-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-15H2,1H3,(H,30,35)(H,31,36)(H,32,33)/t24-/m0/s1
InChI Key
DBJFCKXPEQMMDK-DEOSSOPVSA-N
Canonical SMILES
CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Fmoc-L-Aspartic acid α-7-amido-4-methylcoumarin (Fmoc-L-Asp-AMC) is a peptide derivative commonly used as a substrate in biochemical assays to measure enzymatic activity. This compound combines the Fmoc (9-fluorenylmethoxycarbonyl) protecting group with L-Aspartic acid and an α-7-amido-4-methylcoumarin fluorogenic moiety. The Fmoc group is used to protect the amino group during peptide synthesis, while the α-7-amido-4-methylcoumarin moiety provides fluorescence properties essential for detecting enzymatic activity. The specific structure of Fmoc-L-Asp-AMC allows for the selective cleavage of the peptide bond by certain enzymes, releasing a fluorescent product that can be quantified using spectroscopic methods. This property makes it an invaluable tool in the study and characterization of enzyme function and kinetics.

One of the key industrial applications of Fmoc-L-Asp-AMC is in pharmaceutical research, particularly in drug discovery and development. Researchers utilize this compound to screen potential inhibitors or activators of enzymes involved in disease pathways. By assessing how different compounds affect the cleavage of Fmoc-L-Asp-AMC, scientists can identify new therapeutic agents that modulate enzyme activity, which is crucial for developing novel treatments. This application is vital for accelerating the drug discovery process and improving the efficacy of pharmaceutical products.

Another important application is in the field of biotechnology, where Fmoc-L-Asp-AMC is used in enzyme assays for quality control and process optimization. In biotechnological manufacturing, enzymes play a critical role in various production processes. Fmoc-L-Asp-AMC helps in monitoring enzyme performance and stability, ensuring that bioprocesses are operating efficiently and producing high-quality products. This application helps maintain the consistency and reliability of biotechnological outputs, which is essential for maintaining industry standards.

Fmoc-L-Asp-AMC also finds use in academic research, particularly in studies involving enzyme kinetics and mechanism of action. Researchers use this compound to gain insights into how enzymes function, including their catalytic efficiency and substrate specificity. By measuring the rate of fluorescence increase, scientists can determine enzyme activity and gain a better understanding of the underlying biochemical processes. This knowledge contributes to advancing fundamental biochemistry research and expanding our understanding of enzyme behavior.

Finally, Fmoc-L-Asp-AMC is employed in clinical diagnostics, where it serves as a tool for detecting and quantifying specific enzyme activities in biological samples. This application is crucial for diagnosing various diseases and monitoring patient conditions. By using Fmoc-L-Asp-AMC in diagnostic assays, clinicians can obtain precise measurements of enzyme activity, aiding in disease diagnosis and management. This application highlights the compound's role in bridging research and practical clinical applications, ultimately improving patient care.

1.Synthesis of an amino acid analogue to incorporate p-aminobenzyl-EDTA in peptides.
Song AI1, Rana TM. Bioconjug Chem. 1997 Mar-Apr;8(2):249-52.
A convenient and straightforward synthesis of an amino acid analog, [p-(N-alpha-Fmoc-L-aspartic acid-beta-amido)benzyl]-EDTA tetra-tert-butyl ester, compatible with Fmoc solid phase peptide synthesis strategy is described. This reagent was used to incorporate p-aminobenzyl-EDTA at an internal sequence position in an HIV-1 Tat protein fragment. After cleavage from the resin and standard deprotection, the peptide was purified by high-performance liquid chromatography and characterized by mass spectrometry. Through this methodology, flexible linkers of different lengths and containing various structures can be placed between the alpha-carbon backbone of peptides and metal chelates. These peptides will provide a new class of affinity cleaving reagents that can be directed against protein and nucleic acid targets.
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