Exploring the meaning of sugar configuration in a supramolecular environment: comparison of six octyl glycoside micelles by ITC and NMR spectroscopy

Schmidt-Lassen, Jörn

doi:10.1039/c4md00122b

Cited by 16 publications

(21 citation statements)

References 52 publications

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“…Changes in the relative size of the alkyl‐ or saccharide part influence the aggregation in line with the theory of Israelachvili, and so does changing the spatial orientation of the saccharide head group by modifying the anomeric centre . Introducing different epimers also influences the aggregation behaviour, which is attributed to differences in hydrogen bonding of the alcohol units …”

Section: Introductionsupporting

confidence: 70%

“…Possibly, the small aggregates formed at high temperature act as nucleus for elongation. The minor difference between the temperatures at which the elongation occurs for 1 a and 2 – 4 is surprising because a strong relation between the introduction of different anomers or epimers and the critical micelle concentration (CMC), solubility, and aggregate shape has been observed in alkyl glycosides …”

Section: Resultsmentioning

confidence: 99%

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Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Leenders

Jansen

Frissen

et al. 2016

Chemistry A European J

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Document VersionPublisher's PDF, also known as Version of Record (includes final page, issue and volume numbers)Please check the document version of this publication:• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Abstract: We introduce monosaccharides as versatile watersoluble units to compatibilise supramolecular polymers based on the benzene-1,3,5-tricarboxamide (BTA) moiety with water.Alibrary of monosaccharide-based BTAs is evaluated, varying the length of the alkyl chain (hexyl, octyl, decyl and dodecyl) separating the BTAa nd saccharide units, as well as the saccharideu nits (a-glucose, b-glucose, a-mannose and a-galactose). In all cases, the monosaccharides impart excellent waterc ompatibility. The length of the alkyl chain is the determining factort oo btain either long, one-dimensional supramolecular polymers (dodecyls pacer), small aggregates (decyl spacer) or molecularly dissolved (octyl and hexyl) BTAs in water. For the BTAs comprising ad odecyl spacer, our results suggest that ac ooperative self-assembly process is operative and that the introduction of different monosaccharides does not significantly change the selfassemblyb ehaviour. Finally,w ei nvestigate the potential of post-assembly functionalisation of the formed supramolecular polymers by taking advantage of dynamic covalent bond formation between the monosaccharides and benzoxaboroles. We observe that the supramolecular polymers readily react with af luorescent benzoxaborole derivative permitting imaging of these dynamicc omplexes by confocal fluorescencemicroscopy.

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Section: Introductionsupporting

confidence: 70%

Section: Resultsmentioning

confidence: 99%

Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Leenders

Jansen

Frissen

et al. 2016

Chemistry A European J

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“…Consequence of its amphiphilic nature, the mannoside glycolipids synthesized are able to form aggregates in aqueous solution, and their critical aggregation concentrations, cac , were determined by using both surface tension measurements and fluorescence with ANS as probe. The results obtained for all monoalkyl derivatives studied are shown in Figure , being these values on the order of those reported for similar compounds, particularly for octyl and lauryl derivatives …”

Section: Resultssupporting

confidence: 82%

“…Table summarizes the physical parameters which characterize the aggregates formed by mono‐alkyl derivatives, MXM . The size of aggregates in water, r, obtained by DLS measurements, is particularly high for MLM and MPM , while the value obtained for the octyl derivative MOM , 8.4 nm, is in fair agreement with the 6 nm reported value determined by NMR techniques using Stokes‐Einstein equation . It must be stated that hydrodynamic radius r determined by DLS assumes spherical particles, if not the case, the estimated radius would correspond to the size of the corresponding spherical particle with a diffusion coefficient equal to the actual aggregates.…”

Section: Resultsmentioning

confidence: 55%

“…The magnitude of the critical aggregation concentration is strongly dependent on the stereochemistry of the anomeric center at C4. Higher cac values have been reported for β than for α derivatives, consequence of the direct interaction between the hydroxyl group at C6 with the first methylene group, which results in a decreased hydrophobicity of the alkyl chain . This stereochemical effect can be clearly seen for 3 different monoalkyl monosaccharides (mannoside (Man), glucoside (Glc), and galactoside (Gal)) with cac C 8 αMan ≈ C 8 αGlc < C 8 αGal …”

Section: Resultsmentioning

confidence: 99%

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Alkyl‐mannoside derivatives: Glycolipids able to form big size aggregates

Sandoval-Altamirano

Sánchez

Pizarro

et al. 2018

J of Physical Organic Chem

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Three different series of alkyl mannoside derivatives have been synthesized, designing the hydrophobic portion to provide different topology to the surfactant and, hence, modulating their aggregation properties. The aggregates formed were characterized using both physical and photophysical methodologies, such as surface tension, dynamic light scattering, and emission of selected fluorescent probes. The non‐ionic sugar surfactants have been widely used in studies of membrane solubilization and protein purification. Indeed, mannoside unit, nonionic and hydrophilic, can be selectively recognized by several lectins, which are proteins present in different membranes. Then, the specific interactions of these derivatives incorporated into synthetic bilayers with lectins have been studied and reported. In this work, monoalkyl derivatives with a presumably conical shape and dialkyl derivatives with cylindrical ones, including also a third family with a hydrophilic spacer were studied. These compounds are able to self‐aggregate to form micelle like structures or bilayers despite their topology. Additionally, they are able to form bilayers, using cosurfactants like cholesterol.

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Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides

Wahart,

Dolan,

Anderson

et al. 2023

ChemBioChem

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As the world moves towards net‐zero carbon emissions, the development of sustainable chemical manufacturing processes is essential. Within manufacturing, purification by distillation is often used, however this process is energy intensive and methods that could obviate or reduce its use are desirable. Developed herein is an alternative, oxidative biocatalytic approach that enables purification of alkyl monoglucosides (essential bio‐based surfactant components). Implementing an immobilised engineered alcohol oxidase, a long‐chain alcohol by‐product derived from alkyl monoglucoside synthesis (normally removed by distillation) is selectively oxidised to an aldehyde, conjugated to an amine resin and then removed by simple filtration. This affords recovery of the purified alkyl monoglucoside. The approach lays a blueprint for further development of sustainable alkylglycoside purification using biocatalysis and, importantly, for refining other important chemical feedstocks that currently rely on distillation.

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Exploring the meaning of sugar configuration in a supramolecular environment: comparison of six octyl glycoside micelles by ITC and NMR spectroscopy

Abstract: To promote understanding of sugar configuration in a supramolecular context, glycomicelles were compared and a “trinity projection” of glycosides proposed.

Cited by 16 publications

References 52 publications

Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Alkyl‐mannoside derivatives: Glycolipids able to form big size aggregates

Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides

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