N-Methyl-N-octanoylglucamine

N-辛酰基-N-甲基葡萄糖胺

N-Methyl-N-octanoylglucamine is a chemical compound that inhibits the activity of the enzyme diacylglycerol lipase, which breaks down the lipid diacylglycerol. This leads to an accumulation of diacylglycerols in the cellular membrane and increased permeability of the cell, which results in physiological effects such as increased release of neurotransmitters. N-Methyl-N-octanoylglucamine has been shown to bind to peptides and inhibit their proteolytic degradation by peptidases. It also has been shown to have an effect on monoclonal antibodies with a high affinity for fatty acids. This compound is used for sample preparation prior to analysis by MALDI mass spectrometry.

N-Octanoyl-N-methylglucamine (abbreviated as NMGA) is a non-ionic surfactant that has gained significant attention in various fields of research and industry due to its unique properties and versatile applications. This paper aims to provide a comprehensive review of N-Octanoyl-N-methylglucamine, including its definition, background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, and limitations and future directions.

Definition and Background

NMGA is a derivative of n-dodecyl-β-D-maltoside, commonly used as a substitute for detergents and other surfactants due to its improved solubility and stability. It is an alkylamide that consists of a glucose molecule joined to an eight-carbon chain and a methyl group. NMGA has a hydrophobic tail, which makes it lipophilic, and a glucose head, which makes it hydrophilic, rendering it a non-ionic surfactant.

Physical and Chemical Properties

NMGA is a yellowish liquid or a white solid, depending on its purity. Its molecular formula is C15H31NO6, with a molecular weight of 321.41 Daltons. It has a critical micelle concentration (CMC) of 0.01-0.1 M at 25°C, which is lower than that of other surfactants, indicating its high surface activity. At pH 7, the solubility of NMGA in water is 100 mM, and it does not precipitate even at higher concentrations. NMGA has a low toxicity and can withstand extreme temperatures and pH conditions, making it a reliable surfactant for various applications.

Synthesis and Characterization

NMGA can be synthesized through several methods, but the most common one is the reaction between 8-bromo-octanoic acid and N-methylglucamine. The method involves the alkaline hydrolysis of glycerol to glycerolysis, followed by the reaction of the product with the 8-bromo-octanoic acid to give NMGA. The product is then purified using column chromatography to obtain a pure form of NMGA. The purity of NMGA is normally checked using analytical methods such as TLC, NMR, and HPLC.

Analytical Methods

NMGA can be quantified using various analytical methods. Thin-layer chromatography (TLC) is the most common method for detecting NMGA in samples. The use of high-performance liquid chromatography (HPLC) and ultraviolet (UV) spectrophotometry are often employed in parallel with TLC to improve the limit of detection (LOD) of NMGA.

Biological Properties

NMGA's use in biochemistry often involves its solubilization of membrane proteins due to its ideal properties of being mild and capable of solubilizing proteins at a low critical micelle concentration. The surfactant can also be used to digest membranes and release proteins from them, making it useful for protein assays that require the quantification of particular membrane proteins.

Toxicity and Safety in Scientific Experiments

NMGA is a surfactant with low toxicity compared to other surfactants such as SDS. In most experiments, it is considered non-toxic, and there is no evidence to suggest that NMGA is carcinogenic, teratogenic, or mutagenic. In addition, NMGA can be easily manufactured, and its safety has been adequately established.

Applications in Scientific Experiments

NMGA finds its uses in various fields of research such as in biophysical studies of membrane proteins, and in drug delivery systems, and the production of protein crystals using high-throughput methods of screening. The surfactant is also used to stabilize protein-protein complexes and assist with the purification of proteins from cell extracts.

Current State of Research

Current research indicates that NMGA is an important surfactant in biochemistry that has a promising future. Various companies continue to research the possibilities of using NMGA as a surfactant in the fields of drug discovery, the production of vaccines, and the stabilization of proteins

Potential Implications in Various Fields of Research and Industry

NMGA could have significant implications in various fields of research and industry. Applications that could benefit from NMGAs unique characteristics include its use in the creation of stable vaccine samples and the development of drug discovery regimes.  NMGA’s well know characteristics for protein solubilization and stabilizing properties, making it a potential candidate for protein crystallography in which membrane proteins are used for target-based drug discovery.

Limitations and Future Directions.

NMGA offers many advantages over other surfactants; however, there are still limitations, such as enzyme inhibition and interference with certain assays. Future research could focus on using NMGA in combination with other surfactants to improve its activity where limitations are known. NMGA has been the target of research for drug discovery but also offers potential as a screening method for target selection, such as in fields like vaccine creation. The chemical holds promise for achieving improved protein stabilization and solutions for biochemistry and biophysics problems. The future of N-Octanoyl-N-methylglucamine remains bright, and exploration of its possibilities will lead to greater advancements in various research fields. Additionally, research evaluating NMGA’s unique and known characteristics of solubilization, protein complex stabilization, and enhancing crystallization are ones that can be reevaluating and further investigated.