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

Name: Fmoc-L-glutamic acid α-7-amido-4-methylcoumarin
Brand: BOC Sciences
Rating: 5 (1 reviews)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-002022

CAS number

957311-37-4

Molecular Formula

C30H26N2O7

Molecular Weight

526.54

IUPAC Name

(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(4-methyl-2-oxochromen-7-yl)amino]-5-oxopentanoic acid

Synonyms

Fmoc-L-glutamic acid α-7-amido-4-methylcoumarin; Fmoc-Glu-AMC; n-alpha-(9-fluorenylmethyloxycarbonyl)-l-glutamic acid alpha-(7-amido-4-methylcoumarin)

Appearance

White to off-white crystalline powder

Purity

≥ 99% (HPLC)

Density

1.377±0.06 g/cm3 at 20 °C, 760 mmHg

Melting Point

214-223°C

Boiling Point

845.0±65.0 °C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C30H26N2O7/c1-17-14-28(35)39-26-15-18(10-11-19(17)26)31-29(36)25(12-13-27(33)34)32-30(37)38-16-24-22-8-4-2-6-20(22)21-7-3-5-9-23(21)24/h2-11,14-15,24-25H,12-13,16H2,1H3,(H,31,36)(H,32,37)(H,33,34)/t25-/m0/s1

InChI Key

AMGSEJHFHIETMV-VWLOTQADSA-N

Canonical SMILES

CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CCC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Fmoc-L-glutamic acid α-7-amido-4-methylcoumarin, a specialized reagent with diverse applications in biochemistry, particularly in peptide synthesis and fluorescence studies. Here are four key applications of this compound intricately:

Peptide Synthesis: Serving as a foundational element in solid-phase peptide synthesis, Fmoc-L-glutamic acid α-7-amido-4-methylcoumarin acts as a crucial building block. Its Fmoc-protected group permits the incremental addition of amino acids, facilitating the construction of intricate peptide chains. The presence of a 脽-carboxylic acid side chain offers a functional site for subsequent chemical modifications, enhancing the versatility of synthesized peptides.

Fluorescence Studies: With its coumarin moiety serving as a potent fluorescent tag, this compound finds utility in a myriad of biochemical assays. Upon excitation, it emits a distinctive fluorescent signal, aiding in the tracking of peptides within biological systems. This ability has important implications for elucidating enzyme-substrate interactions and revealing the complexity of the protein folding process.

Drug Discovery: As a pivotal tool in drug development, Fmoc-L-glutamic acid α-7-amido-4-methylcoumarin can be utilized as a substrate for monitoring enzyme activity. By attaching this fluorescent tag to potential drug compounds, researchers can monitor protease or enzyme activity in real-time. This real-time monitoring facilitates the identification of lead compounds and the optimization of drug candidates, catalyzing advancements in pharmaceutical research.

Protein Interaction Studies: Researchers leverage this compound to delve into protein-protein interactions, incorporating it into peptides or protein fragments to elucidate complex molecular interactions. The fluorescent marker embedded within the compound enables the detection and quantification of these interactions under varied conditions. Such insights into protein interactions are pivotal for unraveling intricate cellular processes and designating novel therapeutic targets, underscoring the compound's indispensable role in advancing biomedicine.

1. Acidity characterization of heterogeneous catalysts by solid-state NMR spectroscopy using probe molecules

Anmin Zheng, Shang-Bin Liu, Feng Deng Solid State Nucl Magn Reson. 2013 Oct-Nov;55-56:12-27. doi: 10.1016/j.ssnmr.2013.09.001. Epub 2013 Sep 20.

Characterization of the surface acidic properties of solid acid catalysts is a key issue in heterogeneous catalysis. Important acid features of solid acids, such as their type (Brønsted vs. Lewis acid), distribution and accessibility (internal vs. external sites), concentration (amount), and strength of acid sites are crucial factors dictating their reactivity and selectivity. This short review provides information on different solid-state NMR techniques used for acidity characterization of solid acid catalysts. In particular, different approaches using probe molecules containing a specific nucleus of interest, such as pyridine-d5, 2-(13)C-acetone, trimethylphosphine, and trimethylphosphine oxide, are compared. Incorporation of valuable information (such as the adsorption structure, deprotonation energy, and NMR parameters) from density functional theory (DFT) calculations can yield explicit correlations between the chemical shift of adsorbed probe molecules and the intrinsic acid strength of solid acids. Methods that combine experimental NMR data with DFT calculations can therefore provide both qualitative and quantitative information on acid sites.

2. Simultaneous Quantification of Organic Acids in Tamarillo ( Solanum betaceum) and Untargeted Chemotyping Using Methyl Chloroformate Derivatisation and GC-MS

Chris Pook, Tung Thanh Diep, Michelle Ji Yeon Yoo Molecules. 2022 Feb 15;27(4):1314. doi: 10.3390/molecules27041314.

Sixteen organic acids were quantified in peel and pulp of Amber, Laird's Large and Mulligan cultivars of tamarillo using GC-MS. Fourteen of these compounds had not previously been quantified in tamarillo. An untargeted metabolomics approach was used in parallel to identify and quantify 64 more metabolites relative to the internal standard, indicating abundances of glutamic acid, pro-line, aspartic acid and γ-aminobutyric acid as well as lower concentrations of several other essential fatty acids and amino acids. The main findings were that total organic acid concentration was significantly higher (p < 0.05) in pulp than in peel, with the highest concentration seen in Mulligan pulp (219.7 mg/g DW). Remarkably, after citric acid, the potent bactericide itaconic acid was the second most abundant organic acid. At least 95% of organic acids in tamarillo were one of these two acids, as well as cis-aconitic, malic and 4-toluic acids. Differences between cultivar chemotypes were as substantial as differences between tissues. These results suggest that the bitter flavour of the peel does not result from organic acids. The combination of targeted and untargeted metabolomics techniques for simultaneous qualitative and quantitative investigation of nutrients and flavours is efficient and informative.

3. The Stephan Curve revisited

William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.

The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.