n-Octyl beta-D-thioglucopyranoside

n-Octyl β-D-thioglucopyranoside

Names
IUPAC name (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-octylsulfanyl-oxane-3,4,5-triol
Other names (1S)-Octyl-β-D-thioglucoside
Identifiers
CAS Number	85618-21-9 N
Jmol interactive 3D	Image
PubChem	363418
SMILES CCCCCCCCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
Chemical formula	C14H28O5S
Molar mass	308.434 g/mol
Appearance	Colourless Waxy Semi-Solid
Melting point	125 to 131 °C (257 to 268 °F; 398 to 404 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

n-Octyl β-D-thioglucopyranoside (octylthioglucoside, OTG) is a detergent that is used for cell lysis or to solubilise membrane proteins without denaturing them. This is particularly of use in order to crystallise them or to reconstitute them into lipid bilayers. It has a critical micelle concentration of 9 mM.^[1]

It is an analog of the commonly used detergent octyl glucoside, the presence of the thioether linkage making it resistant to degradation by beta-glucosidase enzymes.

References

External links

• OTG bound to proteins in the PDB