Octyl glucoside

Octyl glucoside (n-octyl-β-d-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".[2]

β-d-Octyl glucoside

Names
IUPAC name (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-octoxyoxane-3,4,5-triol
Other names n-octyl-β-d-glucoside
Identifiers
CAS Number	29836-26-8
3D model (JSmol)	Interactive image
ChemSpider	56585
ECHA InfoCard	100.045.337
EC Number	249-887-8
MeSH	C018619
PubChem CID	62852
UNII	V109WUT6RL
CompTox Dashboard (EPA)	DTXSID6042234
InChI InChI=1S/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14-/m1/s1 Key: HEGSGKPQLMEBJL-RKQHYHRCSA-N InChI=1/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14-/m1/s1 Key: HEGSGKPQLMEBJL-RKQHYHRCBI
SMILES CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
Chemical formula	C14H28O6
Molar mass	292.37 g/mol
Surface tension:
CMC	0.025 M[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[3] Above its critical micelle concentration of 0.025 M[1] (~0.7% w/v), it was noted as the best detergent for improving selectivity of immunoprecipitation of phosphotyrosine modified proteins.[4] This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.[5]

The compound gained popularity with researchers following the publication of an improved synthesis in 1978.[6][7] However, in 1990 the cost remained prohibitive for large-scale protein isolation.[8]

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.[9]

See also

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

External links

• octyl glucoside bound to proteins in the PDB

References

1. Shinoda, Kozo; Yamaguchi, Tokio; Hori, Ryohei (1961). "The Surface Tension and the Critical Micelle Concentration in Aqueous Solution of β-D-Alkyl Glucosides and their Mixtures". Bulletin of the Chemical Society of Japan. 34 (2): 237–241. doi:10.1246/bcsj.34.237.
2. 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 (May 2004). "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. doi:10.1085/jgp.200308996. PMC 2234500. PMID 15111647.
3. Morandat S, El Kirat K (April 2007). "Solubilization of supported lipid membranes by octyl glucoside observed by time-lapse atomic force microscopy". Colloids and Surfaces. B, Biointerfaces. 55 (2): 179–84. doi:10.1016/j.colsurfb.2006.11.039. PMID 17207975.
4. Zhang, G; Neubert, Ta (Jan 2006). "Use of detergents to increase selectivity of immunoprecipitation of tyrosine phosphorylated peptides prior to identification by MALDI quadrupole-TOF MS". Proteomics. 6 (2): 571–8. doi:10.1002/pmic.200500267. ISSN 1615-9853. PMID 16342243.
5. Bosley A, Marshall HN, Badralmaa Y, Natarajan V (Jun 2008). "A method of HIV-1 inactivation compatible with antibody-based depletion of abundant proteins from plasma". Proteomics: Clinical Applications. 2 (6): 904–7. doi:10.1002/prca.200780086. PMID 21136887.
6. See PubMed search for "octyl[Title] AND glucoside[Title]" for a timeline of publications.
7. Keana, Jf; Roman, Rb (1978). "Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry". Membrane Biochemistry. 1 (3–4): 323–7. doi:10.3109/09687687809063854. ISSN 0149-046X. PMID 756493.
8. Kobs, Sf (Nov 1990). "Recovery of octyl beta-glucoside from detergent/protein mixtures". Analytical Biochemistry. 191 (1): 47–9. doi:10.1016/0003-2697(90)90385-M. ISSN 0003-2697. PMID 2077942.
9. Santos L, Rodrigues D, Lira M, Oliveira R, Real Oliveira ME, Vilar EY, Azeredo J (May 2007). "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. doi:10.1097/OPX.0b013e318058a0cc. hdl:1822/6663. PMID 17502827.