N-Octyl-D-glucamine, 正辛基-D-葡萄糖胺

1-Octylamino-1-deoxy-D-glucitol

1-Deoxy-1-(octylamino)-D-glucitol, also known as DOG, is a synthetic compound with structural similarities to glucose. It is widely used as a tool in scientific experiments to investigate the movement of glucose across cell membranes.

Physical and Chemical Properties:

DOGlucitol is a white, odorless, crystalline powder with a molecular weight of 293.40 g/mol. It is soluble in water, methanol, and ethanol but insoluble in non-polar solvents. The compound is stable at room temperature but decomposes on exposure to heat and high humidity.

Synthesis and Characterization:

DOGlucitol can be synthesized in the laboratory by reacting glucose with n-octylamine under controlled conditions. The product is then purified and characterized using standard analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.

Analytical Methods:

Several analytical methods have been used to detect and quantify DOG in biological samples. These methods include high-performance liquid chromatography (HPLC), gas chromatography (GC), and electrochemical detection (ECD).

Biological Properties:

DOG has been shown to inhibit glucose transport across cell membranes, leading to a decrease in cellular glucose uptake. This property makes DOG a useful tool for studying glucose transporters, which are important targets for drug development in diabetes and cancer.

Toxicity and Safety in Scientific Experiments:

Studies have shown that DOG is relatively non-toxic to cells and animals at concentrations used in scientific experiments. However, caution should be taken when handling DOG as it may cause skin and eye irritation.

Applications in Scientific Experiments:

DOG is widely used as a research tool to investigate glucose transport in cells and tissues. It is also used as a negative control in glucose transport assays to evaluate the specificity of glucose transport inhibitors.

Current State of Research:

Recent studies have focused on developing new analytical methods for detecting and quantifying DOG in biological samples. Other studies have explored the potential use of DOG as a therapeutic agent in diabetes and cancer.

Potential Implications in Various Fields of Research and Industry:

The unique properties of DOG make it a valuable tool in biological research. Its inhibitory effect on glucose transporters could be exploited for the development of novel drugs to treat diabetes and cancer. DOG could also find applications in the development of biosensors for glucose monitoring.

Limitations and Future Directions:

Despite its usefulness in scientific experiments, DOG has several limitations that need to be addressed. For example, the compound has limited solubility in organic solvents, which can restrict its use in certain applications. Future research could focus on developing new synthetic routes for DOG and improving its solubility properties. Other possible future directions include exploring the use of DOG as a tool in metabolic labeling and studying its interaction with other biomolecules.

In conclusion, DOG has emerged as a valuable tool in biological research due to its unique properties and applicability in glucose transport studies. Its potential implications span across multiple fields of research and industry, making it a promising candidate for future investigations.

1-Octylamino-1-deoxy-D-glucitol is a natural product that is extracted from the bark of the tree Streptomyces griseorubens. It has been shown to have a diastereomeric ratio of 97:3 and an optical purity of 98%. The thermodynamic properties of this compound are determined by the reaction time, which can vary from 1 to 24 hours. The enantiomers are separated by chromatography or crystallization, and the solubility data is determined at 25°C.

COA:

Product name: N-Octyl-D-glucamine    

M.F.: C₁₄H₃₁NO₅          M.W.: 293.40      CAS: 23323-37-7                   

References:

1. Liu P, Zhu W, Polym. Adv. Technol. 2004, Vol15, No4, p214-217