116183-64-3 ,Alpha-十二烷基-D-麦芽糖苷,
Dodecyl a-D-maltopyranoside,
CAS:116183-64-3
C24H46O11 / 510.62
MFCD00133592
Alpha-十二烷基-D-麦芽糖苷
Dodecyl a-D-maltopyranoside is a solubilized fat that has an optimum pH of 11. It is soluble in chloroform, ethanol, and water. The molecular weight of dodecyl a-D-maltopyranoside is 587.87 g/mol. Dodecyl a-D-maltopyranoside can be used as an absorption marker for lipids in the human liver, wheat germ, and chloroplasts. Dodecyl a-D-maltopyranoside contains two monomers and four subunits. Dodecyl a-D-maltopyranoside can be used to measure the density of lipids in the cell membrane by nmr spectra.
Dodecyl-alpha-D-maltoside (DDM) is a surfactant widely used in various scientific experiments due to its unique properties. Surfactants are molecules that possess both hydrophilic (water-loving) and hydrophobic (water-hating) properties and are capable of reducing surface tension between two immiscible phases. DDM is a non-ionic surfactant that belongs to the group of alkyl maltosides. This paper focuses on the definition and 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, limitations, and future directions related to DDM.
Definition and Background
DDM is a sugar-based detergent composed of a hydrophobic alkyl chain (dodecyl) and a hydrophilic headgroup (maltose). It is commonly utilized in membrane protein research as it is gentle towards proteins and can solubilize them. DDM is different from other commonly used detergents as it can maintain the native state of proteins. It is also used in biophysical studies, where it serves as a membrane mimic.
Physical and Chemical Properties
DDM has a molecular weight of 510.62 g/mol, and its molecular formula is C24H46O11. It appears as a white to off-white crystalline powder and has a melting point of 91-96°C. It is soluble in water, ethanol, and dimethyl sulfoxide (DMSO) but insoluble in chloroform and benzene. Its critical micelle concentration is 0.3-2.5 mM, and the aggregation number is approximately 70-90 molecules.
Synthesis and Characterization
DDM can be synthesized using different methods, such as direct esterification, acylation of glucose, and transglycosylation. The most commonly used method is transglycosylation, which involves using the enzyme cyclodextrin glucanotransferase to transfer the glucose unit from cyclodextrin to a fatty alcohol. The product is then purified using chromatography.
DDM can be characterized using various techniques, including nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), mass spectrometry (MS), and Fourier-transform infrared (FTIR) spectroscopy. NMR spectroscopy is useful in analyzing the structure and purity of the molecule. HPLC and MS can be used to determine the purity and molecular weight of DDM. FTIR spectroscopy is useful in determining the functional groups present in the molecule.
Analytical Methods
The most commonly used technique to detect DDM is HPLC, which can determine the amount and purity of DDM in a sample. Other methods include UV-Vis spectroscopy and electrophoresis.
Biological Properties
DDM has been extensively used in membrane protein research due to its capabilities of gentle protein solubilization and maintenance of protein native state. It is also used in biophysical studies, where it serves as a membrane mimic. Its use in protein solubilization has been compared to other commonly used detergents, such as Triton X-100 and sodium dodecyl sulfate (SDS), and has been shown to maintain the structure and function of the protein. Additionally, DDM can be used to enhance the stability of recombinant proteins.
Toxicity and Safety in Scientific Experiments
DDM is generally considered safe for scientific experiments as it is non-toxic and non-irritating. However, it is recommended to follow good laboratory practices to avoid accidental ingestion, inhalation, or direct exposure to the skin and eyes.
Applications in Scientific Experiments
DDM is commonly used in scientific experiments, especially in membrane protein research and biophysical studies. It is also used as a detergent in biochemical assays, where maintaining the protein's native state is critical. Additionally, it can be used in recombinant protein production to enhance protein stability.
Current State of Research
Research on DDM has grown significantly over the past decade. Most of the research activities have been focused on its applications in membrane protein studies and biophysical studies. There have been studies that compared DDM with other commonly used detergents and its effectiveness in maintaining protein stability. Furthermore, researchers are trying to develop novel derivatives of DDM that can have enhanced properties for biological applications.
Potential Implications in Various Fields of Research and Industry
DDM has the potential to be used in various fields of research, including structural biology, enzymology, and drug discovery. Additionally, its unique properties can be exploited in industrial applications, such as in the development of detergents, medicines, and cosmetics.
Limitations and Future Directions
DDM has some limitations, such as its high cost and limited availability. Researchers are trying to develop cheaper and more accessible alternatives that can mimic DDM's unique properties. Future directions for research on DDM include developing novel derivatives that can have enhanced properties, studying its potential use in drug delivery systems, and exploring its potential in biotechnology.
Conclusion
DDM is a sugar-based surfactant that has unique properties, making it a valuable tool in various scientific experiments. Its gentle protein solubilization and maintenance of protein native state make it a widely-used surfactant in membrane protein research. Its potential use in various fields of research and industry makes it an exciting molecule for further research.
CAS Number | 116183-64-3 |
Product Name | Dodecyl-alpha-D-maltoside |
IUPAC Name | (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-dodecoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C24H46O11 |
Molecular Weight | 510.62 g/mol |
InChI | InChI=1S/C24H46O11/c1-2-3-4-5-6-7-8-9-10-11-12-32-23-21(31)19(29)22(16(14-26)34-23)35-24-20(30)18(28)17(27)15(13-25)33-24/h15-31H,2-14H2,1H3/t15-,16-,17-,18+,19-,20-,21-,22-,23+,24-/m1/s1 |
InChI Key | NLEBIOOXCVAHBD-YHBSTRCHSA-N |
SMILES | CCCCCCCCCCCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O |
Canonical SMILES | CCCCCCCCCCCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O |
Isomeric SMILES | CCCCCCCCCCCCO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O |
CAS No: 116183-64-3 Synonyms: n-Dodecyl a-D-maltosideLauryl a-maltoside MDL No: MFCD00133592 Chemical Formula: C24H46O11 Molecular Weight: 510.62 |
References: 1. VanAken T, Foxall-VanAken S, Castleman S, Ferguson-Miller S, Methods Enzymol. 1986, 125, 27-35 |
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