Octyl-ß-D-Glucopyranosid
Octy1-ß-D-Glucopyranosid hat hervorragende und schonende solubilisierende Eigenschaften und ist daher bestens für die Untersuchung biologischer Membranen geeignet.
Aufgrund seines geringen Molekulargewichts und seiner relativ hohen CMC kann es leicht durch Dialyse oder Gelfiltration aus Solubilisaten entfernt werden.
Octyl-ß-D-glucopyranosid solubilisiert zahlreiche funktionelle Proteine wie Rezeptoren und membrangebundene Enzyme. Die Solubilisierung der Thylakoidmembran höherer Pflanzen unter Aufrechterhaltung des Energietransfers von Chlorophyll b zu Chlorophyll a ist nur eine von vielen Anwendungen.
Octyl-ß-D-glucopyranosid wurde erfolgreich für die funktionelle Rekonstitution von Membranproteinen wie Peptidrezeptoren, ATPasen und Ionenkanal-Komplexen eingesetzt.
OG wird auch zur chromatographischen und elektrophoretischen Auftrennung von Proteinen verwendet; außerdem zur Kristallisation von Proteinen (z.B. Tumor-Nekrose-Faktor) und zur Untersuchung von Protein-Lipid-Wechselwirkungen.
Synonyme: Octylglucosid, OG
CAS-Registriernummer [29836-26-8]
Molekulare Formel: C14H28O6
Relative Molekülmasse (Mr): 292,4
Klassifizierung: Nichtionisches Tensid
Literatur-Spezifikation:
- Kritische mizellare Konzentration (CMC): 25 mM
- Aggregationszahl (Na): 84 (30 °C)
BibliographIE
Rekonstitutionsversuche
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.
Solubilisierung und Charakterisierung von Enzymen
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.
Solubilisierung und Charakterisierung von Rezeptoren
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.
Solubilisierung und Charakterisierung von Photosystemkomponenten
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.
Solubilisierung und Charakterisierung verschiedener Proteine/Proteinkomplexe
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 von Proteinen
Woll, J.M., Hatton, T.A. a. Yarmush, M.L. (1989) Bioaffinity separations using reversed micellar extraction. Biotechnol. Progress 5, 57-62.
Chromatographische und elektrophoretische Auftrennung
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
Weitere Applikationen
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.