Octyl glucoside explained

Octyl glucoside (n-octyl-β--glucoside) is a nonionic surfactant frequently used to solubilise integral membrane proteins for studies in biochemistry. Structurally, it is a glycoside derived from glucose and octanol. Like Genapol X-100 and Triton X-100, it is a nonphysiological amphiphile that makes lipid bilayers less "stiff".^[1]

Applications

Octyl glucoside has become one of the most important detergents for purification of membrane proteins because it generally does not denature the protein and can readily be removed from final protein extracts.^[2] Above its critical micelle concentration of 0.025 M (~0.7% w/v), it was noted as the best detergent for improving selectivity of immunoprecipitation of phosphotyrosine modified proteins.^[3] This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.^[4]

The compound gained popularity with researchers following the publication of an improved synthesis in 1978.^{[5] [6]} However, in 1990 the cost remained prohibitive for large-scale protein isolation.^[7]

Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of contact lenses, due to its ability to lower the hydrophobicity of contact lenses and prevent adhesion of Staphylococcus epidermidis and Pseudomonas aeruginosa.^[8]

See also

• Decyl glucoside
• Lauryl glucoside
• Alkyl polyglycoside
• octyl thioglucoside

External links

• octyl glucoside bound to proteins in the PDB

Notes and References

1. Lundbaek JA, Birn P, Hansen AJ, Søgaard R, Nielsen C, Girshman J, Bruno MJ, Tape SE, Egebjerg J, Greathouse DV, Mattice GL, Koeppe RE, Andersen OS . Regulation of sodium channel function by bilayer elasticity: the importance of hydrophobic coupling. Effects of Micelle-forming amphiphiles and cholesterol . The Journal of General Physiology . 123 . 5 . 599–621 . May 2004 . 15111647 . 2234500 . 10.1085/jgp.200308996 .
2. Morandat S, El Kirat K . Solubilization of supported lipid membranes by octyl glucoside observed by time-lapse atomic force microscopy . Colloids and Surfaces. B, Biointerfaces . 55 . 2 . 179–84 . April 2007 . 17207975 . 10.1016/j.colsurfb.2006.11.039 .
3. 16342243 . Jan 2006 . Zhang, G . Neubert, Ta . Use of detergents to increase selectivity of immunoprecipitation of tyrosine phosphorylated peptides prior to identification by MALDI quadrupole-TOF MS . 6 . 2 . 571–8 . 1615-9853 . 10.1002/pmic.200500267 . Proteomics. 26930507 .
4. 21136887 . Jun 2008 . Bosley A, Marshall HN, Badralmaa Y, Natarajan V . A method of HIV-1 inactivation compatible with antibody-based depletion of abundant proteins from plasma. . 2 . 6 . 904–7 . 10.1002/prca.200780086 . Proteomics: Clinical Applications. 19247865 .
5. See PubMed search for "octyl[Title] AND glucoside[Title]" for a timeline of publications.
6. 756493 . 1978 . Keana, Jf . Roman, Rb . Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry . 1 . 3–4 . 323–7 . 0149-046X . Membrane Biochemistry . 10.3109/09687687809063854.
7. 2077942 . Nov 1990 . Kobs, Sf . Recovery of octyl beta-glucoside from detergent/protein mixtures . 191 . 1 . 47–9 . 0003-2697 . Analytical Biochemistry . 10.1016/0003-2697(90)90385-M.
8. Santos L, Rodrigues D, Lira M, Oliveira R, Real Oliveira ME, Vilar EY, Azeredo J . The effect of octylglucoside and sodium cholate in Staphylococcus epidermidis and Pseudomonas aeruginosa adhesion to soft contact lenses . Optometry and Vision Science . 84 . 5 . 429–34 . May 2007 . 17502827 . 10.1097/OPX.0b013e318058a0cc . 1822/6663 . 2509161 . free .