59122-55-3Relevant articles and documents
The Synthesis and Micellar Properties of a Novel Anionic Surfactant
Jones, Rose F. D.,Camilleri, Patrick,Kirby, Anthony J.,Okafo, George N.
, p. 1311 - 1312 (1994)
The synthesis is described of dodecyl β-D-glucopyranoside-6-phosphate, a novel surfactant possessing a long-chain hydrocarbon tail and a hydrophilic head consisting of a phosphoryl group covalently linked to a (homochiral) glucose moiety; this compound, which forms micelles at concentrations above 0.25 mmol dm-3, has been successfully used in micellar electrokinetic capillary chromatography for the separation of a variety of analytes, including enantiomers.
Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition
Sabah, Karem J.,Zahid, N. Idayu,Hashim, Rauzah
, p. 2653 - 2667 (2021/03/19)
A series of new mix aza- and thia-macrocyclic glycolipids (9, 10, 16 and 17) have been synthesized and their enantiomeric selectivity was studied. The synthesis of the macrocycles involved a simple protection of two hydroxyl groups of the glycolipids followed by building up the mix-heteroatom macrocyclic in simple sequences. The macrocycles and previously investigated analogues (18, 19, 20 and 21) have been applied as phase transfer catalysts in the enantioselective Michael addition of 2-nitropropane to chalcone and showed good-to-excellent enantiomer excess (ee). Among the catalysts, the galactose aza-crown ether-based glycolipid 21 proved to be the most effective with 90% ee. Graphic abstract: [Figure not available: see fulltext.]
Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
Bogdanová, Kate?ina,Combet, Sophie,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marian,Kanjaková, Nina,Klunda, Tomá?,Kolá?, Milan,Poláková, Monika,Uhríková, Daniela
, (2020/01/30)
A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.
Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons
Ramdani, Wahiba Ghezali,Karam, Ayman,De Oliveira Vigier, Karine,Rio, Sébastien,Ponchel, Anne,Jér?me, Fran?ois
, p. 125 - 129 (2019/03/06)
Herein we investigated the catalytic performances of sulfonated mesoporous carbons in the glycosylation of carbohydrates with alkyl alcohols. Catalytic performances were compared to common solid acid catalysts previously reported for this reaction. Under optimized conditions, the targeted alkyl glycosides were obtained in 85% yield, together with a turn over frequency and a space time yield higher than those of the best heterogeneous catalysts reported so far in such reaction. Furthermore, the presence of mesoporous channels significantly lowered the deactivation rate of the catalyst in comparison to a non-porous sulfonated carbon.
Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles
Voggel, Michael,Meinusch, Rebecca M.,Siewert, Vanessa,Kunkel, Marius,Wittmann, Valentin,Polarz, Sebastian
, p. 7214 - 7227 (2018/09/26)
Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.
N-alkyl - β - D - glucopyranoside synthetic method
-
Paragraph 0029; 0030; 0034; 0036, (2017/12/06)
The invention discloses a synthesizing method of n-alkyl-beta-D-glucopyranoside. The method includes the following steps of dissolving fully-acetylated glucopyranose, n-alkyl alcohol and anhydrous stannic chloride in anhydrous methylene dichloride, stirring the mixture to have a reaction for 20 min to 70 min at the room temperature, washing the mixture through a saturated sodium carbonate solution, collecting organic phases, conducting reduced pressure distillation to obtain 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside, dissolving the 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside in methyl alcohol, adding sodium methylate to adjust the pH value to 9, having a reaction for 1.5 h at the room temperature, adjusting the pH value to be neutral through strong acid cation exchange resin, conducting filtering, steaming filtrate to obtain solvent, and drying the solvent to obtain the n-alkyl-beta-D-glucopyranoside. The n-alkyl is n-alkyl of C8-C12. The method is simple, raw materials are easy to obtain, cost is low, reaction temperature is moderate and easy to control, the method is environmentally friendly, and the prepared beta-configuration glucopyranoside is high in purity.
Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum
De Winter, Karel,Van Renterghem, Lisa,Wuyts, Kathleen,Pelantová, Helena,K?en, Vladimír,Soetaert, Wim,Desmet, Tom
, p. 1961 - 1969 (2015/06/02)
Abstract Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous α-glucosides. In contrast, much less research has been done with respect to the production of β-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENGTM 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various β-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl β-D-glucopyranosides, also the formation of vanillyl 4-O-β-D-glucopyranoside, 2-phenylethyl β-D-glucopyranoside, β-citronellyl β-D-glucopyranoside and 1-O-β-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl β-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl β-D-glucopyranoside.
Novel mixed-heteroatom macrocycles via templating: A new protocol
Sabah, Karem J.,Hashim, Rauzah
, p. 1534 - 1537 (2013/03/14)
A series of novel thiadiaza and triaza crown ether attached galactose- and glucose-based glycolipids is synthesized, applying a new strategy. The key step is the formation of α-chloroacetamido precursors (14 and 21) from selectively protected bis(cyanomethyl)-glycolipids (13 and 19) in two steps. The cyclization reaction furnishes good yields in relatively short times in aqueous ethanol or acetonitrile. To generalize this method, macrocycles 3 and 25 are reported as well. Attempts to use the traditional synthetic approaches for cyclization failed to provide reasonable yields.
A novel type of highly effective nonionic gemini Alkyl O-glucoside surfactants: A nersatile strategy of design
Liu, Songbai,Sang, Ruocheng,Hong, Shan,Cai, Yujing,Wang, Hua
, p. 8511 - 8516 (2013/07/26)
A novel type of highly effective gemini alkyl glucosides has been rationally designed and synthesized. The gemini surfactants have been readily prepared by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery.
The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone
Song, Shao-Xing,Wu, Ming-Li,He, Xiao-Peng,Zhou, Yu-Bo,Sheng, Li,Li, Jia,Chen, Guo-Rong
supporting information; experimental part, p. 2030 - 2032 (2012/04/23)
The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.
