Octyl glucoside

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β-D-Octyl glucoside
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Names
IUPAC name
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-octoxyoxane-3,4,5-triol
Other names
n-octyl-β-D-glucoside
Identifiers
29836-26-8 YesY
ChemSpider 56585 N
EC Number 249-887-8
Jmol 3D model Interactive image
MeSH C018619
PubChem 62852
  • 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 N
    Key: HEGSGKPQLMEBJL-RKQHYHRCSA-N 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
  • CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
C14H28O6
Molar mass 292.37 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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]

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

External links

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ See PubMed search for "octyl[Title] AND glucoside[Title]" for a timeline of publications.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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