59080-45-4Relevant articles and documents
Synthesis of glycotriazololipids and observations on their self-assembly properties
Tyagi, Mohit,Kartha, K.P. Ravindranathan
supporting information, p. 85 - 92 (2015/06/30)
Abstract Various carbohydrate-anchored triazole-linked lipids prepared by solvent-free mechanochemical azide-alkyne click reaction, on analysis by TEM, have been found to spontaneously self-assemble in solvents leading to structures of interesting physicochemical attributes. Interestingly, analogous compounds based on different sugars (e.g., d-glucose, and d-galactose, as also d-lactose) assemble in patterns distinctly different from each other thus reiterating the fact that the structure of the sugar as well as that of the lipid are important factors that determine the size and shape of the supramolecular assembly formed. Besides, the molecular self-assembly was also found to be solvent-as well as temperature-dependent.
Preparation of two glycoside hydrolases for use in micro-aqueous media
Lundemo, Pontus,Karlsson, Eva Nordberg,Adlercreutz, Patrick
, p. 1 - 6 (2014/07/22)
Enzymatic synthesis of alkyl glycosides using glycoside hydrolases is well studied, but has yet to reach industrial scale, primarily due to limited yields. Reduced water content should increase yields by limiting the unwanted hydrolytic side reaction. However, previous studies have shown that a reduction in water content surprisingly favors hydrolysis over transglycosylation. In addition, glycoside hydrolases normally require a high degree of hydration to function efficiently. This study compares six enzyme preparation methods to improve resilience and activity of two glycoside hydrolases from Thermotoga neapolitana (TnBgl3B and TnBgl1A) in micro-aqueous hexanol. Indeed, when adsorbed onto Accurel MP-1000 both enzymes increasingly favored transglycosylation over hydrolysis at low hydration, in contrast to freeze-dried or untreated enzyme. Additionally, they displayed 17-70× higher reaction rates compared to freeze-dried enzyme at low water activity, while displaying comparable or lower activity for fully hydrated systems. These results provide valuable information for use of enzymes under micro-aqueous conditions and build toward utilizing the full synthetic potential of glycoside hydrolases.
Significantly improved equilibrium yield of long-chain alkyl glucosides via reverse hydrolysis in a water-poor system using cross-linked almond meal as a cheap and robust biocatalyst
Wang, Qinqqin,Yu, Huilei,Zhao, Na,Li, Chunxiu,Shang, Yazhuo,Liu, Honglai,Xu, Jianhe
, p. 275 - 280 (2012/06/29)
An array of ten β-D-glucopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl β-D-glucoside increased from 1.9 to 6.1 when the water content was reduced from 10 to 5 (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl β-D-glucoside was found to have significant surface activity as well.
