85618-20-8

Usage

Uses

Used in Biochemistry Research:
N-HEPTYL-BETA-D-THIOGLUCOPYRANOSIDE is used as a solubilizing agent for membrane proteins, specifically for the solubilization and reconstitution of membrane proteins of Escherichia coli. It is particularly useful in biochemical research, where the study of membrane proteins is crucial for understanding various cellular processes and developing potential therapeutic agents.
Used in Pharmaceutical Industry:
N-HEPTYL-BETA-D-THIOGLUCOPYRANOSIDE is used as a reconstitution agent for membrane proteins in the pharmaceutical industry. Its ability to maintain the integrity of membrane proteins makes it a valuable tool in drug discovery and development, as it allows researchers to study the interactions between membrane proteins and potential drug candidates.
Used in Structural Biology:
N-HEPTYL-BETA-D-THIOGLUCOPYRANOSIDE is used as a detergent in structural biology for the crystallization of membrane proteins. Its non-ionic nature and ability to solubilize membrane proteins make it an ideal choice for facilitating the formation of protein crystals, which are essential for determining the three-dimensional structure of proteins using X-ray crystallography.

Purification Methods

The tetraacetyl derivative is purified by silica gel column chromatography and eluted with a *C6H6/Me2CO gradient (up to 5% of Me2CO) and recrystallises from n-hexane as colourless needles m 72-74o (Erbing & Lindberg Acta Chem Scand B30 611 1976 gave m 69-70o). Hydrolysis with an equivalent of base in methanol gives the desired glucoside. This is a non-ionic detergent for reconstituting membrane proteins and has a critical micelle concentration of 30 mM. [Shimamoto et al. J Biochem (Tokyo) 97 1807 1985; Saito & Tsuchiya Chem Pharm Bull Jpn 33 503 1985].

InChI:InChI=1/C13H26O5S/c1-2-3-4-5-6-7-19-13-12(17)11(16)10(15)9(8-14)18-13/h9-17H,2-8H2,1H3/t9-,10-,11+,12-,13+/m1/s1

Upstream product

• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 1639-09-4 heptanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 629-04-9 1-Bromoheptane 
• 61198-95-6 n-heptyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Highly β-Selective Glycosylation Reactions for the Synthesis of ω-Functionalized Alkyl β-Maltoside as a Co-crystallizing Detergent

Abstract: Methods have been reported for the preparation of ω-functionalized alkyl maltoside and glycoside detergents via a simple and inexpensive synthetic route. The key step was stannic chloride-mediated glycosylation of long-chain alcohols or thiols with maltose octaacetate at 0 or –10°C, respectively, within a very short time (isolated yield 17–44%), which provided more than 98% β-selectivity.

Synthesis and surface properties of alkyl β?D?thioglucopyranoside

Alkyl thioglycosides are a class of nonionic sugar-based sulfur-containing surfactants and bioreagents. The surfactants 1,2?trans alkyl β?D?thioglucopyranosides with different alkyl chain length (n = 6–12) were stereoselectively prepared by the Helferich method. Their properties including HLB number, logP value, water solubility, foam property, emulsifying property, surface property and thermotropic liquid crystal property were mainly investigated. The results showed that their HLB numbers and water-solubility decreased as the related logP values increased with increasing the alkyl chain length. Alkyl β?D?thioglucosides were already insoluble in water with n ≥ 10. Both β?D?thioglucopyranosides (n = 8, 9) reduced the surface tension of the related aqueous solution to nearly 29 mN·m?1 at the critical micelle concentration (CMC), they also had excellent foaming ability and foam stability. Nonyl β?D?thioglucopyranoside had good emulsifying properties for both n?octane/water system and toluene/water system. Alkyl β?D?thioglucopyranosides (n = 6–12) were observed to have the thermotropic liquid crystal properties.

Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-D-glycopyranosides

This paper describes the synthesis, purification, and liquid- crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2. The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S(A) phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety.

Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R′ on the 4,6-O-ylidene β-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R′ for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

Synthesis of Alkyl-β-D-thioglucopyranosides, a Series of New Nonionic Detergents

As a part of our search for new types of detergent useful for biological applications, a series of alkyl-β-D-thioglucopyranosides was synthesized in several steps from glucose.The overall yield was about 80percent.Critical micelle concentrations of n-hexyl-, n-heptyl-, n-octyl-, and n-nonyl-β-D-thioglucopyranoside were determined.Because of their electroneutrality, high solubility in water and high critical micelle concentration, n-heptyl- and n-octyl-β-D-thioglucopyranoside seem to be potentially useful detergents for applications in biological systems.