imported>JCW-CleanerBot: /* Applications */ task, replaced: Colloids and Surfaces. B, Biointerfaces → Colloids and Surfaces B: Biointerfaces

2024-10-09T16:42:31Z

Applications: task, replaced: Colloids and Surfaces. B, Biointerfaces → Colloids and Surfaces B: Biointerfaces

New page

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 401570012
| Name = β-{{small|D}}-Octyl glucoside
| ImageFile = octyl glucoside.png
| ImageSize = 200px
| IUPACName = Octyl β-{{small|D}}-glucopyranoside
| SystematicName = (2''R'',3''S'',4''S'',5''R'',6''R'')-2-(Hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
| OtherNames = ''n''-Octyl-β-{{small|D}}-glucoside
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 29836-26-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V109WUT6RL
| PubChem = 62852
| SMILES = CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
| EINECS = 249-887-8
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 56585
| 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
| InChIKey = HEGSGKPQLMEBJL-RKQHYHRCBI
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HEGSGKPQLMEBJL-RKQHYHRCSA-N
| RTECS =
| MeSHName = C018619
}}
|Section2={{Chembox Properties
| Formula=C14H28O6
| MolarMass=292.37 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
| CMC =0.025 [[Molar concentration|M]]<ref name=cmc>{{cite journal|last1=Shinoda|first1=Kozo|last2=Yamaguchi|first2=Tokio|last3=Hori|first3=Ryohei|title=The Surface Tension and the Critical Micelle Concentration in Aqueous Solution of β-D-Alkyl Glucosides and their Mixtures|journal=Bulletin of the Chemical Society of Japan|date=1961|volume=34|issue=2|pages=237–241|doi=10.1246/bcsj.34.237|doi-access=free}}</ref>
| HLB =
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}

'''Octyl glucoside''' ('''''n''-octyl-β-{{sm|d}}-glucoside''') is a [[nonionic surfactant]] frequently used to solubilise [[integral membrane protein]]s 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 bilayer]]s less "stiff".<ref name="pmid15111647">{{cite journal | vauthors = 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 | title = Regulation of sodium channel function by bilayer elasticity: the importance of hydrophobic coupling. Effects of Micelle-forming amphiphiles and cholesterol | journal = The Journal of General Physiology | volume = 123 | issue = 5 | pages = 599–621 | date = May 2004 | pmid = 15111647 | pmc = 2234500 | doi = 10.1085/jgp.200308996 }}</ref>

==Applications==
Octyl glucoside has become one of the most important detergents for purification of membrane proteins because it generally does not [[Denaturation (biochemistry)|denature]] the protein and can readily be removed from final protein extracts.<ref name="pmid17207975">{{cite journal | vauthors = Morandat S, El Kirat K | title = Solubilization of supported lipid membranes by octyl glucoside observed by time-lapse atomic force microscopy | journal = Colloids and Surfaces B: Biointerfaces | volume = 55 | issue = 2 | pages = 179–84 | date = April 2007 | pmid = 17207975 | doi = 10.1016/j.colsurfb.2006.11.039 }}</ref> Above its [[critical micelle concentration]] of 0.025 M<ref name=cmc /> (~0.7% w/v), it was noted as the best detergent for improving selectivity of [[immunoprecipitation]] of [[phosphotyrosine]] modified proteins.<ref>{{cite journal | pmid = 16342243 |date=Jan 2006 |author1=Zhang, G |author2=Neubert, Ta | title = Use of detergents to increase selectivity of immunoprecipitation of tyrosine phosphorylated peptides prior to identification by MALDI quadrupole-TOF MS | volume = 6 | issue = 2 | pages = 571–8 | issn = 1615-9853 | doi = 10.1002/pmic.200500267 | journal = Proteomics|s2cid=26930507 }}</ref> This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.<ref>{{cite journal | pmid = 21136887 |date=Jun 2008 | vauthors = Bosley A, Marshall HN, Badralmaa Y, Natarajan V | title = A method of HIV-1 inactivation compatible with antibody-based depletion of abundant proteins from plasma. | volume = 2 | issue = 6 | pages = 904–7 | doi = 10.1002/prca.200780086 | journal = Proteomics: Clinical Applications|s2cid=19247865 }}</ref>

The compound gained popularity with researchers following the publication of an improved synthesis in 1978.<ref>See [https://www.ncbi.nlm.nih.gov/sites/entrez PubMed] search for "octyl[Title] AND glucoside[Title]" for a timeline of publications.</ref><ref>{{cite journal | pmid = 756493 | year = 1978 |author1=Keana, Jf |author2=Roman, Rb | title = Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry | volume = 1 | issue = 3–4 | pages = 323–7 | issn = 0149-046X | journal = Membrane Biochemistry | doi=10.3109/09687687809063854}}</ref> However, in 1990 the cost remained prohibitive for large-scale protein isolation.<ref>{{cite journal | pmid = 2077942 |date=Nov 1990 | author = Kobs, Sf | title = Recovery of octyl beta-glucoside from detergent/protein mixtures | volume = 191 | issue = 1 | pages = 47–9 | issn = 0003-2697 | journal = Analytical Biochemistry | doi = 10.1016/0003-2697(90)90385-M}}</ref>

Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of [[contact lens]]es, due to its ability to lower the [[hydrophobicity]] of contact lenses and prevent adhesion of ''[[Staphylococcus epidermidis]]'' and ''[[Pseudomonas aeruginosa]]''.<ref name="pmid17502827">{{cite journal | vauthors = Santos L, Rodrigues D, Lira M, Oliveira R, Real Oliveira ME, Vilar EY, Azeredo J | title = The effect of octylglucoside and sodium cholate in Staphylococcus epidermidis and Pseudomonas aeruginosa adhesion to soft contact lenses | journal = Optometry and Vision Science | volume = 84 | issue = 5 | pages = 429–34 | date = May 2007 | pmid = 17502827 | doi = 10.1097/OPX.0b013e318058a0cc | hdl = 1822/6663 | s2cid = 2509161 | hdl-access = free }}</ref>

==See also==
* [[Decyl glucoside]]
* [[Lauryl glucoside]]
* [[Alkyl polyglycoside]]
* [[OTG (n-octyl beta-D-thioglucopyranoside)|octyl thioglucoside]]

==External links==
* [http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=BOG octyl glucoside bound to proteins] in the [[Protein Data Bank|PDB]]

== References ==
{{reflist}}

[[Category:Glucosides]]
[[Category:Non-ionic surfactants]]
[[Category:Octyl compounds]]

Octyl glucoside - Revision history

imported>JCW-CleanerBot: /* Applications */ task, replaced: Colloids and Surfaces. B, Biointerfaces → Colloids and Surfaces B: Biointerfaces