n-Dodecyl-β-D-maltoside

n-Dodecyl-β-D-maltoside

n-Dodecyl-β-D-maltoside (CAS No. 69227-93-6) is a non-ionic surfactant and glycoside widely utilized in biochemical and biophysical research, particularly for the solubilization and stabilization of membrane proteins.

Chemical and Physical Properties

• CAS Number: 69227-93-6
• MDL Number: MFCD00043012
• EINECS: Not specified
• Molecular Formula: C₂₄H₄₆O₁₁
• Molecular Weight: 510.62 g/mol
• Boiling Point: 703.5 °C at 760 mmHg
• Melting Point: 224–226 °C
• Flash Point: 379.3 ± 32.9 °C
• Density: 1.28 g/cm³
• Appearance: Off-white powder

Structure and Composition

n-Dodecyl-β-D-maltoside consists of a dodecyl group attached to the anomeric carbon of maltose, forming a glycosidic bond. This structure imparts amphiphilic properties, allowing it to interact with both hydrophilic and hydrophobic environments.

Biological Activity and Applications

1. Membrane Protein Research: n-Dodecyl-β-D-maltoside (DDM) is extensively used for isolating and purifying membrane proteins, including G-protein coupled receptors (GPCRs) and ion channels, while preserving their structural integrity and functionality.
2. Stabilization of Enzymes: It is effective in stabilizing enzymes such as RNA polymerase, enhancing their activity during biochemical assays.
3. Detection of Protein-Lipid Interactions: DDM facilitates the study of interactions between proteins and lipids, providing insights into membrane dynamics.
4. Cryo-Electron Microscopy and X-ray Crystallography: Its mild nature makes it suitable for structural studies where maintaining protein conformation is critical.

Synthesis Methods

The synthesis of n-Dodecyl-β-D-maltoside typically involves the glycosylation of maltose with dodecanol in the presence of an acid catalyst or through enzymatic methods that promote the formation of glycosidic bonds.

Safety and Handling

While generally considered safe for laboratory use, standard safety protocols should be followed to avoid skin or eye contact.

Storage Recommendations

For optimal long-term stability, store this compound at 2–8°C in a cool, dry place, protected from light and moisture.

In summary, n-Dodecyl-β-D-maltoside is a versatile non-ionic detergent essential for membrane protein research and various biochemical applications, providing a means to study complex biological systems without compromising protein integrity.

Citations:

1. https://avantiresearch.com/product/850520
2. https://www.sigmaaldrich.com/IN/en/product/sigma/d4641
3. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8191322.htm
4. https://www.avantorsciences.com/us/en/product/17468639/n-dodecyl-beta-maltoside-detergent-thermo-scientific
5. https://en.wikipedia.org/wiki/Maltoside
6. https://www.dojindo.com/ASIA/products/D316/
7. https://pubchem.ncbi.nlm.nih.gov/compound/114880
8. https://www.medchemexpress.com/n-dodecyl-beta-d-maltoside.html