Synthesis and properties of some α-D-alkyl glucosides and mannosides: apparent molal volumes and solubilization of nitrobenzene in water at 25 °C

Abstract

Normal and cyclic a-D-alkyl glucosides and mannosides have been synthesized in a one-step procedure from the corresponding sugar. The apparent molal volume and the influence on the solubility of nitrobenzene of some of these glycosides have been measured in water at 25 "C. Evidence for micelle formation is presented for a-D-11-hexyl glucoside, -11-octyl glucoside, and -cyclohexyl mannoside. Comparison of the physical properties of the aqueous solutions shows that the stereochemistry of the sugar unit plays an important role in the hydrophobic hydration and hydrophobic interactions of the glycosides.Canadian Journal of Chemistry, 48, 2525Chemistry, 48, (1970 IntroductionThe investigation of thermodynamic and kinetic properties of aqueous solutions of homologous series such as the salts RNH,Br (1-3) has proven to be very useful in the understanding of hydrophobic interactions between organic ions in the submicellar region. The general objective of the present work was to extend these studies to non-ionic systems. In this respect, solutes such as alkyl glycosides are of particular interest because, in addition to their potential biological and pharmaceutical applications, they furnish a means of investigating the influence of the polar group on the solute-solvent and solute-solute interactions.Despite the very large number of possible isomers, the only work reported, to our knowledge, on the solution properties of such systems is on the surface tension of octyl, decyl, and dodecyl P-D-glucosides (4, 5). We have chosen to study the normal and cyclic alkyl a-D-glucosides and mannosides. Fewer a-D-than P-D-glycosides are known in the literature, and we felt that there was a possibility of preparing them using a one-step experimental procedure from the corresponding sugars, in spite of the fact that it is customary in the synthesis of a-D-glucosides to use a multistep process. A rCsumt of synthetic methods has been given by Wing and BeMiller (6).The properties investigated were apparent molalvolumes and solubilization of nitrobenzene. Apparent molal volumes are very informative since, in addition to defining the region over which a micelle is formed, this property is very sensitive to solute-solvent and solute-solute interactions. The choice of nitrobenzene as a

Zeta Potential of Nanobubbles Generated by Ultrasonication in Aqueous Alkyl Polyglycoside Solutions

“…Table 1. Values proposed in several published reports are within a similar range (17)(18)(19)(20)(21). The concentration of each AGs is about 3 times the critical micelle concentration.…”

Molecular Recognition of Pyranosides by a Family of Trimeric, 1,1′-Binaphthalene-Derived Cyclophane Receptors

“…Commercially available guests were used without further treatment. Pyranosides 50 [69] and 54 [70] were prepared according to published procedures. The host concentration was kept constant at 0.5 mm, and a soln.…”

Fourier transform infrared spectroscopic study of ion binding and intramolecular interactions in the polar head of digalactosyldiacylglycerol

“…Based on filling model studies and conformational analysis data (Brown et al 1970;Jarrell et al 1987), Mannock et al (1990) suggested that (i) the band at 1 715 cm-1 exhibited by the fl-anomer originated from hydrogen bonding between the 2-hydroxyl of the sugar moiety and the sn 2 C = O, and (ii) the configuration of the e-anomeric centre would not permit H-bond-256 ing interactions. These conclusions show the importance of intramolecular hydrogen bonding in the geometrical arrangement and the polymorphic phase behavior of bilayers composed of glycolipids.…”