Alkyl Xylosides: Physico‐Chemical Properties and Influence on Environmental Bacteria Cells

Abstract

A group of four selected non-ionic surfactants based on carbohydrates, namely octyl d-xyloside (C8X), nonyl d-xyloside (C9X), decyl d-xyloside (C10X) and dodecyl d-xyloside (C12X), have been investigated to accomplish a better understanding of their physico-chemical properties as well as biological activities. The surface-active properties, such as critical micelle concentration (CMC), emulsion and foam stability, the impact of the compounds on cell surface hydrophobicity and cell membrane permeability together with their toxicity on the selected bacterial strains have been determined as well. The studied group of surfactants showed high surface-active properties allowing a decrease in the surface tension to values below 25 mN m−1 for dodecyl d-xyloside at the CMC. The investigated compounds did not have any toxic influence on two Pseudomonas bacterial strains at concentrations below 25 mg L−1. The studied long-chain alkyl xylosides influenced both the cell inner membrane permeability and the cell surface hydrophobicity. Furthermore, the alkyl chain length, as well as the surfactant concentration, had a significant impact on the modifications of the cell surface properties. The tested non-ionic surfactants exhibited strong surface-active properties accompanied by the significant influence on growth and properties of Pseudomonas bacteria cells.

Solution Properties of Alkyl β‐D‐Maltosides

“…However, there are not enough data and messages available to support effectively the application in the field of life and material sciences although there are some available features/parameters including critical micelle concentration (CMC) (Frotscher et al, 2017;Matsuoka et al, 2017;Santonicola et al, 2008), sugar headgroup structure (Ehsan et al, 2016), field-induced phase transition (Hashim et al, 2017), paracellular permeation (Gradauer et al, 2017), and cell metabolism (Smułek et al, 2017). The corresponding fairly accurate and feasible screening should rely heavily on the empirical evidence, exhaustive trial-and-error process and rational thinking, and even intuitive approach.…”

“…Based on their bigger hydrophilic disaccharide headgroups, alkyl D‐maltosides should have higher water solubility than that of alkyl D‐glucosides with the same alkyl chain length. Alkyl D‐maltosides with a longer alkyl chain length would improve the surface properties (for example micelle size) to a certain extent as a class of sugar‐based surfactants/detergents available for the related research and applications (Smułek et al, ). For the α‐anomer and β‐anomer micelles with dodecyl group tails, the computed radii of gyration were 20.2 and 25.4 Å, respectively.…”

Simultaneous Improvement of Final Product-Tolerance and Thermostability of GH39 Xylosidase for Prebiotic Production by Directed Evolution

“…), which largely hinders their largescale practical application in industry. In addition, good thermostability is also required for industrial applications, since high process temperatures can reduce the possibility of microbial contamination and decrease the production cost [10]. It is therefore of great significance to develop xylosidases with high product tolerance and good thermostability.…”

Water Solubility and Surface Property of Alkyl Di-/Tri-/Tetraoxyethyl β-d-Xylopyranosides

“…Alkyl (poly)­glycosides (APGs) are a type of environmentally friendly non-ionic surfactant, which contain a hydrophilic glycosyl head and a hydrophobic alkyl tail. − As a new type of green non-ionic surfactant, APGs and the related anomerically pure 1,2- cis or 1,2- trans alkyl glycosides (AGs) have the following features: low surface activity, good foamability, good thickening effect, low/no toxicity, low/no irritation, complete biodegradation, good compatibility with skin, mildness in the formulation, strong alkaline resistance, and excellent caustic stability. − They are widely used in daily cosmetics, the food processing industry, pharmaceuticals, etc. − However, APGs are easy to crystallize and precipitate under low temperatures. Also, their water solubility decreases with increasing the alkyl chain length, and they even have not water solubility with a longer alkyl chain. , At the same time, their structure–property−performance relationship is rather ambiguous and uncertain as a result of their mixtures of homologues, anomers, and isomers.…”

“…The water solubility of alkyl d -glycopyranosides, as one of the wind vanes of sugar-based surfactants in the practical application, is closely related to their configuration. Decyl α- d -glucopyranoside, dodecyl β- d -glucopyranoside, dodecyl oxyethyl β- d -glucopyranoside, and hexadecyl tri­(oxyethyl) oligooxyethyl β- d -glucopyranoside , had no water solubility, whereas nonyl d -xyloside and octyl β- d -xylopyranoside had no water solubility. Therefore, alkyl β- d -xylopyranoside ( 12 ) needs to improve .…”