128299-95-6Relevant academic research and scientific papers
Molecular recognition of carbohydrates by zinc porphyrins: Lewis acid/Lewis base combinations as a dominant factor for their selectivity
Mizutani, Tadashi,Kurahashi, Takuya,Murakami, Takeshi,Matsumi, Noriyoshi,Ogoshi, Hisanobu
, p. 8991 - 9001 (1997)
A systematic study of the binding of carbohydrates by functionalized zinc porphyrins indicated that [5,15-bis(8-quinolyl)porphyrinato]zinc(II) (1) showed marked affinity for octyl glucoside and mannoside in CHCl3 (-ΔG°= 4.5-6.3 kcal mol-1
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.
Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents
Manhas, Sanjay,Taylor, Mark S.
, p. 11406 - 11417 (2017/11/10)
Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived boronic esters provides results that are qualitatively consistent with the observed distributions of furanoside versus pyranoside products. The boronic esters that are obtained as direct products of these reactions serve as protected intermediates for the synthesis of functionalized glycosides. Complexation of particular diol groups by the boronic acid also enables selective transformations of mixtures of carbohydrates.
Exploring the meaning of sugar configuration in a supramolecular environment: Comparison of six octyl glycoside micelles by ITC and NMR spectroscopy
Schmidt-Lassen, J?rn,Lindhorst, Thisbe K.
supporting information, p. 1218 - 1226 (2014/08/05)
A series of octyl α- and β-glycosides of the manno- galacto- and gluco-series were synthesized and employed in formation of homo- and hetero-micelles in water. Critical micelle concentrations (cmc), thermodynamic quantities of demicellation and, to some extent, the hydrodynamic radii of glycomicelles were determined by isothermal titration calorimetry (ITC) and diffusion NMR studies. The goal of this work was to determine the significance of anomeric configuration as well as of epimerisation at the sugar ring for supramolecular features of the respective glycoside. A new projection of glycoside structures is proposed to facilitate interpretation of structure-property relationships in this regard. This journal is the Partner Organisations 2014.
Synthesis of alkyl and cycloalkyl α-D-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay
Polakova, Monika,Belanova, Martina,Petrus, Ladislav,Mikusova, Katarina
experimental part, p. 1339 - 1347 (2010/10/02)
The synthesis of a series of alkyl (having from C6 to C20 aglycones), cyclohexyl, and cyclohexylalkyl α-Dmannopyranosides, 6-deoxygenated analogs, thioglycosides, and sulfones derived thereof, is reported. Here, under the in vitro assay conditions used, n
Rapid, iterative assembly of octyl α-1,6-oligomannosides and their 6-deoxy equivalents
Watt, Jacinta A.,Williams, Spencer J.
, p. 1982 - 1992 (2007/10/03)
Mycobacterium tuberculosis is the cause of the deadly human disease tuberculosis. In studies over the last 40 years it has been revealed that this organism possesses a complex cell wall including glycophospholipids such as the phosphatidylinositiol mannos
Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases
Ziegler, Thomas,Dettmann, Ralf,Duszenko, Michael,Kolb, Volker
, p. 7 - 23 (2007/10/03)
Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure α-D-Manp-(1→2)-α-D-Manp-(1→6)-α-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D -mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic α-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MITat 1.4, MITat 1.2, and MITat 1.5, respectively.
