Introduction of a Series of Alkyl Thiomaltosides, Useful New Non-Ionic Detergents, to Membrane Biochemistry1

Abstract

We synthesized a series of non-ionic detergents, alkyl thiomaltosides, and investigated their properties and usefulness. We solubilized membrane proteins of Vibrio parahaemolyticus using the detergents. With octyl thiomaltoside, nonyl thiomaltoside, decyl thiomaltoside, or undecyl thiomaltoside, we observed satisfactory solubilization of the membrane proteins. Alkyl thiomaltosides possessing longer alkyl chains showed better solubilization than ones possessing shorter chains. H(+)-translocating ATPase (F0F1), which is localized in the cytoplasmic membrane (inner membrane), was solubilized with the detergents, and the solubilized enzyme showed much higher specific activity than that solubilized with octyl glucoside or heptyl thioglucoside, other useful non-ionic detergents. 5'-Nucleotidase, which seems to be an outer membrane protein, was also efficiently solubilized with the alkyl thiomaltosides. Membrane proteins of Escherichia coli were also efficiently solubilized with the detergents. Octyl thiomaltoside and nonyl thiomaltoside were removed fairly rapidly on dialysis. Decyl thiomaltoside was removed slowly, and undecyl thiomaltoside and dodecyl thiomaltoside were difficult to remove by dialysis.

Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

“…In the last few years, therefore, odorless methods for preparing thioglycosides have received much attention. 4 Even earlier, in 1993, Tsuchiya reported 5 that dodecyl 1-thio-β-maltoside prepared from 1-dodecanethiol was used as a non-ionic detergent for biological applications. Stimulated by this work, we prepared various dodecyl thioglycosides and examined their properties in glycosylation reactions.…”

Dodecyl thioglycopyranoside sulfates: Novel sugar‐based surfactants for enantiomeric separations by micellar electrokinetic capillary chromatography

“…Since carbohydrates are readily available with various structural analogues and with both D-and L-enantiomers, combination with sugar head groups and hydrophobic alkyl chains would have a potential to construct a library of chiral surfactants. Although various thioglycosides have used for either solubilization membrane proteins or synthetic intermediates [22][23][24], few investigations have been performed to apply thioglycosides to MEKC analyses. Under this situation, we undertook to examine the applicability of thioglycosides to enantiomeric separation by MEKC.…”

Interaction of octyl-beta-thioglucopyranoside with lipid membranes

“…The thioether has a better chemical stability than its oxygen analog, octyl-,B-D-glucopyranoside (octyl glucoside, OG), and is not degraded by f3-D-glucosidase. The high stability of the thioether bond has induced the synthesis of thiomaltosidecontaining surfactants (Izawa et al, 1993). The critical micellar concentration of OTG has been determined as -9 mM (in water) Brackman et al, 1988) compared to 20-25 mM for OG (Antonelli et al, 1994;Paula et al, 1995), suggesting that OTG is a more hydrophobic amphiphile than OG.…”