Octyl glucoside (''n''-octyl-β--glucoside) is a
nonionic surfactant
Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foami ...
frequently used to solubilise
integral membrane proteins for studies in
biochemistry
Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...
. Structurally, it is a
glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
derived from
glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...
and
octanol
Octanols are alcohols with the formula C8H17OH. A simple and important member is 1-octanol, with an unbranched chain of carbons. Other commercially important octanols are 2-octanol and 2-ethylhexanol.
There are 89 possible isomers
In ch ...
. Like
Genapol X-100 and
Triton X-100, it is a nonphysiological
amphiphile
An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compoun ...
that makes
lipid bilayers less "stiff".
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.
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
Immunoprecipitation (IP) is the technique of precipitating a protein antigen out of solution using an antibody that specifically binds to that particular protein. This process can be used to isolate and concentrate a particular protein from a samp ...
of
phosphotyrosine
-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Gr ...
modified proteins. This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.
The compound gained popularity with researchers following the publication of an improved synthesis in 1978. However, in 1990 the cost remained prohibitive for large-scale protein isolation.
Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of
contact lens
Contact lenses, or simply contacts, are thin lenses placed directly on the surface of the eyes. Contact lenses are ocular prosthetic devices used by over 150 million people worldwide, and they can be worn to correct vision or for cosmetic ...
es, due to its ability to lower the
hydrophobicity of contact lenses and prevent adhesion of ''
Staphylococcus epidermidis
''Staphylococcus epidermidis'' is a Gram-positive bacterium, and one of over 40 species belonging to the genus '' Staphylococcus''. It is part of the normal human microbiota, typically the skin microbiota, and less commonly the mucosal microbio ...
'' and ''
Pseudomonas aeruginosa
''Pseudomonas aeruginosa'' is a common encapsulated, gram-negative, aerobic–facultatively anaerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, ''P. aerugi ...
''.
See also
*
Decyl glucoside
Decyl glucoside is a mild non-ionic surfactant used in cosmetic formularies,Fiume MM, Heldreth B, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler D, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Andersen FA. Safety assessment of decyl gluco ...
*
Lauryl glucoside
Lauryl glucoside is a surfactant used in cosmetics and laundry detergents. It is a glycoside produced from glucose and lauryl alcohol.
See also
* Decyl glucoside
Decyl glucoside is a mild non-ionic surfactant used in cosmetic formularies,F ...
*
Alkyl polyglycoside
Alkyl polyglycosides (APGs) are a class of non-ionic surfactants widely used in a variety of cosmetic, household, and industrial applications. Biodegradable and plant-derived from sugars, these surfactants are usually glucose derivatives, and fat ...
*
octyl thioglucoside
External links
octyl glucoside bound to proteinsin the
PDB
References
{{reflist
Glucosides
Non-ionic surfactants