Octyl-ß-D-Glucopyranoside

Octy1-ß-D-glucopyranoside has excellent and gentle solubilizing properties and is therefore best suited for investigation of biological membranes.
Due to its small molecular weight and its relatively high CMC, it can easily be removed from solubilizates by dialysis or gel filtration.

Octyl-ß-D-glucopyranoside solubilizes numerous functional proteins like receptors and membrane-bound enzymes. The solubilization of the thylakoid membrane of higher plants whilst maintaining the energy transfer from chlorophyll b to chlorophyll a is only one of many applications.
Octyl-ß-D-glucopyranoside has been succcessfully used for the functional reconstitution of membrane proteins like peptide receptors, ATPases and ion channel complexes.
OG is also used for chromatographic and electrophoretic separation of proteins; furthermore for crystallization of proteins (e.g. tumor necrosis factor) and for investigation on protein-lipid interactions.

Synonyms: Octylglucoside, OG

CAS registry number [29836-26-8]

Molecular formula: C14H28O6

Relative molecular mass (Mr): 292.4

Classification: Non-ionic surfactant

Literature specification:
•    Critical micellar concentration (CMC): 25 mM
•    Aggregation number (Na): 84 (30 °C)


Bibliography

Reconstitution Experiments

Hirata, H. (1988) Reconstitution of ion channels into planar phospholipid bilayers. Ferro-electrics 86, 115-20.

Patemostre, M. T., Roux, M. a. Rigaud, J.L. (1988) Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (prepared by reverse-phase evaporation) by Triton X-100, octyl glucoside, and sodium cholate. Biochemistry 27, 2668-77.

Cupo, J.F., Allen, R.A., Jesaitis, A. a. Bokoch, G.M. (1989) Reconstitution and characterization of the human neutraphil N-formyl peptide receptor and GTP binding proteins in phospholipid vesicles. Biochim. Biophys. Acta 982, 31-40.

Maloney, P.C., Ambudkar, S.V. (1989) Functional reconstitution of prokaryote and eukaryote membrane proteins. Arch. Biochem. Biophys. 269, 1-10.

Rossignol, M., Kervella, V. a. Blein, J.P. (1989) Octylglucoside reconstitution of plasma membrane hydrogen ion-translocating ATPase from corn roots. Plant Physiol. Biochem. 27, 437-41.

Zimmerman, D.L. a. Walter, P. (1990) Reconstitution of protein translocation activity from par¬tially solubilized microsomal vesicles. J. Biol. Chem. 265, 4048-53.

Fricke, B. et al. (1993) Membrane-bound proteinases of Halobacterium halobium. J. Basic Mirobiol. 33, 9-18.

Kobayashi, M. et al. (2004) Reconstitution and replacement of bacteriochlorophyll a molecules in photosynthetic reaction centers. J. Biochem. 136, 363-9.

Pedersen, M.O. et al. (2008) A reconstituted light-harvesting complex from the green sulfur bacterium Chloobium tepidum containing CsmA and bacteriochlorophyll a. Biochemistry 47, 1435-41.

Solubilization and Characterization of Enzymes

Lippo de Becemberg, I., Pena de Aguilar, A.E., Camarillo, I., Gonzalez de Alfonzo, R. a. Alfonzo, M. (1989) Muscarinic agents modify kinetic properties of membrane-bound guanylyl cyclase activity. FEBS Lett. 253, 16-22.

Saha, A.K., Dowling, J.N., Mukhopadhyay, N.K. a. Glew, R.H. (1989) Legionella micdadei protein kinase catalyzes phosphorylation of tubulin and phosphatidylinositol. J. Bacteriol. 171, 5103-10.

Zou, L., Kojima, N , Kito, M. a. Yagi, K. (1989) Purification to homogeneity of human placental acid sphingomyelinase. Biotechnol. Appl. Biochem. 11, 217-25.

Kerner, J. a. Bieber, L. (1990) Isolation of a malonyl-CoA-sensitive CPT/ß-oxidation enzyme complex from heart mitochondria. Biochemistry 29, 4326-34.

Ota, Y. et al. (2003) Assay method for mitochondrial sterol 27-hydroxylase with 7α-hydroxy-4-cholesten-3-one as a substrate in the rat liver. J. Lipid Res. 44, 2400-5.

Linke, T. et al. (2005) Isolation and characterization of a microsomal acid retinyl ester hydrolase. J. Biol. Chem. 280, 23287-94.

Al-Dabbagh, B. et al. (2008) Purification and characterization of the bacterial UDP-GlcNAc:undecaprenyl-phosphate GlcNAc-1-phosphate transferase WecA. J. Bacteriol. 190, 7141-6.

Solubilization and Characterization of Receptors

Henley, J.M. a. Barnard, E.A. (1989) Solubilization and characterization of a putative quisqualate-type glutamate receptor from chick brain. J. Neurachem. 53. 140-8.

Krah, D.L. (1989) Characterization of octyl glucoside-solubilized cell membrane receptors for binding measles virus. Virology 172, 386-90.

Schuerholz, T., Gieselmann, A. a. Neumann, E. (1989) Miscibility gap of octyl glucoside-phosphatidylcholine micellar solutions. Partition of the nicotinic acetylcholine receptor into the surfactant-rich phase. Biochim. Biophys. Acta 986, 225-33.

Inui, A. et al. (1992) Solubilization of the receptors for avian pancreatic polypeptide in chicken, canine, and pig brains. Endocrinology 130, 3314-22.

Solubilization and Characterization of Photosystem Components

Sukenik, A., Falkowski, P.G. a. Bennett, J. (1989) Energy transfer in the light-harvesting complex II of Dunaliella tertiolecta is unusually sensitive to Triton X-100. Photosynth. Res. 21, 37-44.

Gast, P. et al. (1994) Determination of the number of detergent molecules associated with the reaction center protein isolated from the photosynthetic bacterium Rhodopseudomonas viridis. Effects of the amphiphilic molecule 1,2,3-heptanetriol. FEBS Lett. 337, 39-42.

Bergantino, E. et al. (2003) Light- and pH-dependent structural changes in the PsbS subunit of photosystem II. PNAS 100, 15265-70.

Camm, E.L. et al. (2004) How the chlorophyll-proteins got their names. Photosynth. Res. 80, 189-96.

Dewa, T. et al. (2005) Design and expression of cystein-bearing hydrophobic polypeptides and their self-assembling properties with bacteriochlorophyll a derivatives as a mimic of bacterial photosynthetic antenna complexes. Effect of steric confinement and orientation of the polypeptides on the pigment/polypeptide assembly process. Biochemistry 44, 5129-39.

Suzuki, H. et al. (2007) Purification, characterization and crystallization of the core complex from thermophilic purple sulphur bacterium Thermochromatium tepidum. Biochim. Biophys. Acta (Bioenergetics) 17671057-63.

Solubilization and Characterization of Various Proteins/Protein Complexes

Cordoba, J., Reboiras, M.D. a. Jones, M.N. (1988) Interaction of n-octyl-ß-D-glucopyranoside with globular proteins in aqueous solution. Int. J Biol. Macromol. 10, 270-6.

Jacobs, E., Fuchte, K. a. Bredt, W. (1988) Isolation of the adherence protein of Mycoplasma pneumoniae by fractionated solubilization and size exclusion chromatography. Biol. Chem. Hoppe-Seyler 369, 1295-99.

Mascher, E. a. Lundahl, P. (1988) The human red cell glucose transporter in octyl glucoside. High specific activity of monomers in the presence of membrane lipids. Biochim. Biophys. Acta 945, 350-9.

Welling-Wester, S., Haring, R.M., Laurens, H., Oervell, C. a. Welling, G. W. (1988) Comparison of ion-exchange high-performance liquid chromatography columns for purification of Sendai virus integral membrane proteins. J. Chromatogr. 476, 477-85.

De Pinto, V., Benz, R. a. Palmieri, F. (1989) interaction of non-classical detergents with the mitochondrial porin. A new purification procedure and characterization of the pore-forming unit. Eur. J. Biochem. 183, 179-87.

Walker, N., Marcinowski, S., Hillen, H.,Maechtle, W., Jones, Y. a. Stuart, D. (1990) Crystallization of human tumor necrosis factor. J. Cryst. Growth 100, 168-70.

Bellovino, D. et al. (1996) Retinol binding protein and transthyretin are secreted as a complex formed in the endoplasmic reticulum in HepG2 human hepatocarcinoma. Exp.Cell Res. 222, 77-83.

Pergami, P. et al. (1996) Semipreparative chromatographic method to purify the normal cellular isoform of the prion protein in nondenatured form. Anal. Biochem. 238, 63-73.

Kalus, I. et al. (2002) Interaction of syncollin with GP-2, the major membrane protein of pancreatic zymogen granules, and association with lipid microdomains. Biochem. J. 362, 433-42.

Mo, C. et al. (2002) Protein-protein interactions among C-4 demethylation enzymes involved in yeast sterol biosynthesis. PNAS 99, 9739-44.

Reversed Micellar Extraction of Proteins

Woll, J.M., Hatton, T.A. a. Yarmush, M.L. (1989) Bioaffinity separations using reversed micellar extraction. Biotechnol. Progress 5, 57-62.

Chromatographic and Electrophoretic Separation

Hierten, S., Valtcheva, L., Elenbring, K. a. Eaker, D. (1989) High-performance electrophoresis of acidic and basic low-molecular-weight compounds and of proteins in the presence of polymers and neutral surfactants, J. Liq. Chromatogr. 12, 2471-99.

St-Martin, M. a. Paquin, P. (1990) Ion-exchange fast protein liquid chromatography: optimization of the purification of caseins using a non-denaturing detergent J. Dairy Res. 57, 63-8.

Linke, T. et al. (2005) Isolation and characterization of a microsomal acid retinyl ester hydrolase. J. Biol. Chem. 280, 23287-94.

Kimberley, A. et al. (2007) System of Shigella dysenteriae. Substrate specifity and identification of the heme protein ligands. J. Biol. Chem. 282, 15126-36

Further Applications

Tomich, J.M., Carson, L.W., Kanes, K.J., Vogelaar, N.J., Emerling, M.R., a.Richards, J.H. (1988) Prevention of aggregation of synthetic membrane-spanning peptides by addition of detergent. Anal. Biochem. 174, 197-203.

Kunimoto, M., Shibata, K. a. Miura, T. (1989) Comparison of the cytoskeleton fractions of rat blood cells prepared with non-ionic detergents. J. Biochem. 105, 190-5.

Merza, MS., Linne, T., Hoeglund, S., Portetelle, D., Burny, A. a. Morein, B. (1989) Bovine leukemia virus ISCOMs: biochemical characterization. Vaccine 7, 22-8.

Shiao, Y.J.,    Chen, J.C. a. Wang, C.T. (1989) The solubilization and morphological change in human platelets in various detergents. Biochim. Biophys. Acta 980, 56-68.

Ueno, M. (1989) Partition behavior of a nonionic detergent, octyl glucoside, between membrane and water phases, and its effect on membrane permeability. Biochemistry 28, 5631-4.

Wallsten, M., Yang, Q. a. Lundahl, P. (1989) Entrapment of lipid vesicles and membrane protein-lipid vesicles in gel bead pores. Biochim. Biophys. Acta 982, 47-52.

Lasch, J., Hoffmann, J., Omelyanenko, V.G., Klibanov, A.A., Torchilin, V.P., Binder, H. a. Garwisch, K. (1990) Interaction of Triton X-100 and octyl glucoside with liposomal membranes at sublytic and lytic concentrations. Spectroscopic studies. Biochim. Biophys. Acta 1022, 171-80.

Park, H.H. et al. (2003) Effect of nonionic n-octyl-ß-D-glucopyranoside surfactant on the stability improvement of silver polymer electrolyte membranes for olefin/paraffin separation. J. Membrane Sci. 217, 285-93.

Garner, A.E. et al. (2008) Visualization of detergent solubilization of membranes: implications for the isolation of rafts. Biophys. J. 94, 1326-40.


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