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Application Area

Acetyl-DL-glutamic acid

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

Category

DL-Amino Acids

Catalog number

BAT-003570

CAS number

5817-08-3

Molecular Formula

C7H11NO5

Molecular Weight

189.17

IUPAC Name

2-acetamidopentanedioic acid

Synonyms

Ac-DL-Glu-OH; 2-acetamidopentanedioic acid; N-Acetyl-DL-glutamic acid

Appearance

White to off-white powder

Purity

≥ 98% (HPLC)

Density

1.354±0.06 g/cm3(Predicted)

Melting Point

178-182 °C

Boiling Point

495.9±35.0 °C(Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)

InChI Key

RFMMMVDNIPUKGG-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC(CCC(=O)O)C(=O)O

Acetyl-DL-glutamic acid is a synthetic derivative of glutamic acid, where the amino group of glutamic acid is acetylated, creating an ester bond with an acetyl group. This modification enhances the compound's stability, solubility, and reactivity compared to the parent amino acid. Acetyl-DL-glutamic acid is commonly used in various biochemical and pharmaceutical applications, serving as a versatile intermediate for further synthesis and as a reagent in research. It is particularly valuable for studying the effects of acetylation in biological processes.

One key application of Acetyl-DL-glutamic acid is in peptide synthesis. The acetyl group protects the amino group of glutamic acid, making it an effective tool for creating peptides and proteins with modified or stabilized glutamic acid residues. By using Acetyl-DL-glutamic acid, researchers can manipulate the peptide structure to enhance stability, bioactivity, and solubility. This is especially useful in drug development, where peptides with specific biological activities need to be synthesized for therapeutic purposes.

Another important application is in the modification of glutamate receptors. Acetyl-DL-glutamic acid serves as a tool for studying the role of glutamic acid derivatives in neurotransmitter pathways, particularly in the context of excitatory neurotransmission. Researchers use it to investigate how modifications to glutamic acid affect receptor binding and signal transduction. This is valuable in understanding the mechanisms underlying neurological conditions, such as epilepsy, Alzheimer's, and Parkinson's disease, where glutamate signaling is often disrupted.

Acetyl-DL-glutamic acid is also employed in the development of prodrugs. By attaching an acetyl group to glutamic acid, the molecule becomes more lipophilic, improving its ability to cross cellular membranes. This property is particularly useful for enhancing the bioavailability of drugs that would otherwise be poorly absorbed. Once inside the body, the acetyl group can be cleaved, releasing the active glutamic acid or its derivatives. This strategy is used to optimize the pharmacokinetics of drugs, particularly for conditions requiring targeted delivery.

Finally, Acetyl-DL-glutamic acid is used in the synthesis of biocompatible materials, particularly for drug delivery systems and tissue engineering. The acetylation of glutamic acid provides a means to modify the physical properties of polymers derived from glutamic acid. These materials can be designed for controlled release of therapeutic agents, offering advantages in the development of drug delivery systems for long-term treatment and in the creation of scaffolds for tissue regeneration. This makes it a valuable compound in both medical and biotechnological applications.

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. 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.

3. Dietary Acid Load Associated with Hypertension and Diabetes in the Elderly

Tulay Omma, Nese Ersoz Gulcelik, Fatmanur Humeyra Zengin, Irfan Karahan, Cavit Culha Curr Aging Sci. 2022 Aug 4;15(3):242-251. doi: 10.2174/1874609815666220328123744.

Background: Diet can affect the body's acid-base balance due to its content of acid or base precursors. There is conflicting evidence for the role of metabolic acidosis in the development of cardiometabolic disorders, hypertension (HT), and insulin resistance (IR). Objective: We hypothesized that dietary acid load (DAL) is associated with adverse metabolic risk factors and aimed to investigate this in the elderly. Methods: A total of 114 elderly participants were included in the study. The participants were divided into four groups, such as HT, diabetes (DM), both HT and DM, and healthy controls. Anthropometric, biochemical, and clinical findings were recorded. Potential renal acid load (PRAL) and net endogenous acid production (NEAP) results were obtained for three days, 24-hour dietary records via a nutrient database program (BeBiS software program). Results: The groups were matched for age, gender, and BMI. There was a statistically significant difference between the groups regarding NEAP (p =0.01) and no significant difference for PRAL ( p = 0.086). The lowest NEAP and PRAL levels were seen in the control group while the highest in the HT group. Both NEAP and PRAL were correlated with waist circumference (r = 0,325, p = 0.001; r=0,231, p =0,016, respectively). Conclusion: Our data confirmed that subjects with HT and DM had diets with greater acid-forming potential. High NEAP may be a risk factor for chronic metabolic diseases, particularly HT. PRAL could not be shown as a significantly different marker in all participants. Dietary content has a significant contribution to the reduction of cardiovascular risk factors, such as HT, DM, and obesity.