C14H28O6 / 292.37
OCTYL B-GLUCOSIDE;N-OCTYL-BETA-D-GLC;CAPRYLYL GLUCOSIDE;β-D-Octyl Glucoside;OCTYL BETA-GLUCOSIDE
Octyl beta-D-glucopyranoside is an alkylglycoside non-ionic detergent and is one of the most commonly used in membrane protein isolation. As it is uncharged, it is unlikely to cause protein denaturation or refolding issues, allowing for the isolation of intact macromolecular complexes without affecting protein-protein interactions. Octyl b-D-glucopyranoside, also known as octylglucoside or OG, forms small, uniformed micelles and has an aggregation number of between 27-100. It is readily dialyzable from membrane protein preparations due to its high Critical Micelle Concentration (CMC) of 18-20mM. Octyl b-D-glucopyranoside has similar uses and properties to that of another frequently used surfactant.
Non-ionic detergent. Solubilizes membrane-bound proteins. Permeabilizes cell membranes of paraformaldehyde fixed cells. Forms self-assembled nanostructures in water.
n-Octylglucoside is a mild, non-denaturing detergent that is used for the solubilization and reconstitution of membrane-bound proteins. The high critical micelle concentration (0.7%) of n-octylglucoside facilitates ready removal from final protein extracts by dialysis or gel filtration. n-Octylglucoside can be used in 2D electrophoresis and to improve selectivity of immunoprecipitation of phosphotyrosine modified proteins.
Octyl beta-D-glucopyranoside (OGP) is an alkyl glucoside often used in biology and biochemistry. It is a non-ionic detergent commonly used in purification and reconstitution of membrane proteins (1). OGP has a b-C8 alkyl chain attached to the first carbon of D-glucose. The octyl group is hydrophobic, while the glucoside (glucose) group is hydrophilic, making the molecule amphipathic (2). This unique structure makes OGP an ideal candidate for solubilizing membrane proteins while preserving their native structure.
1. Definition and Background
OGP is a surfactant commonly used in biochemical and biological research. It is a member of the alkyl glycoside family, which are non-ionic surfactants, characterized by a carbohydrate head group linked to a hydrophobic alkyl chain. OGP is stable in a range of temperatures and pH values and is compatible with biological systems, making it a popular choice for membrane protein purification (3).
2. Physical and Chemical Properties
OGP has a chemical formula of C14H28O6 and a molecular weight of 292.37 g/mol. It is a white crystalline powder with a melting point of 90-95°C (4). OGP is soluble in water and alcohols and slightly soluble in non-polar solvents such as chloroform and ether. OGP has a critical micelle concentration (CMC) of approximately 250 μM (5).
3. Synthesis and Characterization
OGP can be synthesized through a condensation reaction between glucose and octyl alcohol in the presence of an acid catalyst. The resulting product is purified by column chromatography and recrystallized from ethanol to obtain pure OGP (6). OGP can be characterized using various spectroscopic techniques such as nuclear magnetic resonance (NMR), infrared spectroscopy, and mass spectrometry.
4. Analytical Methods
OGP can be quantified using various analytical techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and spectrophotometry. These methods can be used to determine the purity of OGP and monitor its concentration during purification or reconstitution of membrane proteins (7).
5. Biological Properties
OGP is widely used as a non-ionic detergent for solubilizing and stabilizing membrane proteins. It has been shown to preserve the activity and structure of many membrane proteins, including G protein-coupled receptors (GPCRs), ion channels, and transporters (8). OGP has also been used to improve protein crystallization and increase membrane protein yield (9).
6. Toxicity and Safety in Scientific Experiments
OGP is generally considered safe for use in scientific experiments. It is biocompatible and has low toxicity, making it a suitable replacement for other harsher detergents such as sodium dodecyl sulfate (SDS) (10). However, like all chemicals, OGP should be handled with care. Inhalation, ingestion, or skin contact can cause irritation and harm and should be avoided.
7. Applications in Scientific Experiments
OGP is widely used in biochemistry and structural biology research. Its most common application is for solubilizing and stabilizing membrane proteins. It has also been used in protein crystallization, lipid extraction, and liposome production (11).
8. Current State of Research
OGP continues to be widely used in biochemical and biological research. Many studies have focused on improving the stability of membrane proteins and discovering new drugs that target membrane proteins. Recently, OGP has been used in cryo-electron microscopy (cryo-EM) studies to solve the structures of membrane proteins, including GPCRs and ion channels (12).
9. Potential Implications in Various Fields of Research and Industry
OGP has potential implications in many fields of research and industry. It can be used in biotechnology to improve the production of enzymes and proteins for industrial use. It may also have potential applications in drug development, particularly for the development of drugs that target membrane proteins.
10. Limitations and Future Directions
Despite its versatile applications, OGP does have limitations. It may not be suitable for all types of membrane proteins and may require optimization of conditions for optimal solubility and stability. Future research should focus on expanding the use of OGP for the solubilization of difficult-to-study membrane proteins. Additionally, further studies are needed to explore the potential use of OGP in drug development and other fields of biotechnology.
1. Further studies on the use of OGP in combination with other detergents to enhance solubilization and stability of membrane proteins.
2. Exploration of the use of OGP in gene therapy and drug delivery applications.
3. Investigation of the potential for OGP to be used in the production of nanomaterials for various applications.
4. Development of new analytical methods for the characterization of OGP, including mass spectrometry-based methods.
5. Further studies on the toxicology and safety of OGP for use in biomedical applications.
6. Exploration of the potential of OGP as an alternative to other surfactants in various industrial applications.
7. Studies on the use of OGP in the production of biofuels and other bioproducts.
8. The development of new OGP derivatives to expand its applications in various fields.
9. Further studies on the use of OGP in cryo-EM studies to reveal the structure and function of membrane proteins.
10. The optimization of OGP for drug development applications focusing on membrane protein targets.
In conclusion, Octyl beta-D-glucopyranoside is a versatile detergent that has various applications in the fields of biochemistry and structural biology research. It is essential for the solubilization and stabilization of membrane proteins, making it a useful tool for the study of membrane biology and the development of new drugs. However, further research is needed to fully explore the potential of OGP.
CAS Registry Number: 29836-26-8
CAS Name: Octyl-b-D-glucopyranoside
Additional Names: n-octylglucoside; OG
Molecular Formula: C14H28O6
Molecular Weight: 292.37
Percent Composition: C 57.51%, H 9.65%, O 32.83%
Literature References: Nonionic detergent primarily used for solubilizing membrane-bound proteins. Prepn: C. R. Noller, C. W. Rockwell, J. Am. Chem. Soc. 60, 2076 (1938). Partition behavior between water and membrane phases: M. Ueno, Biochemistry 28, 5631 (1989); thermodynamics and structural impact: M. R. Wenk et al., Biophys. J. 72, 1719 (1997). Solubilzation and reconstitution of liposomes: O. López et al., J. Phys. Chem. B 105, 9879 (2001). Solubilization of lipid vesicles: A. Meister, A. Blume, Phys. Chem. Chem. Phys. 6, 1551 (2004). Micelle formation: A. Walter et al., Biochim. Biophys. Acta 1508, 20 (2000); in mixed systems: A. Lainez et al., Langmuir 20, 5745 (2004).
Properties: White solid, mp 65-99°. [a]D25 -30.3° (methanol). Critical micelle concentration: 20-25 mM.
Melting point: mp 65-99°
Optical Rotation: [a]D25 -30.3° (methanol)
Use: Detergent and surfactant for biological systems.
CAS No: 29836-26-8
Synonyms: n-Octylglucoside1-O-Octyl b-D-glucopyranosideOGCaprylyl glucoside
MDL No: MFCD00063288
Chemical Formula: C14H28O6
Molecular Weight: 292.37
Normally more than 100kg available in stock.
1. Gould RJ, et.al., Biochemistry, 1981, 20, p6776
2. Lorber B, Bishop JB, Delucas L, J. Biochim. Biophys. Acta, 1990, 1023, p254-265
3. Conlan S, Bayley H, Biochemistry, 2003, 42, p9453-9465
4. Jopski B, et.al., Biochim. Biophys. Acta, 1989, 978, 79
5. Fanucci GE, Lee JY, Cafiso DS, Biochemistry 2003, 42, p13106-13112
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