Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators.

ABSTRACT: Low molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators are interesting soft materials that show great potential for many applications. Previously, we have synthesized a series of methyl 4,6-O-benzylidene-α-D-glucopyranoside derivatives and found that several of them are good gelators for water, aqueous mixtures of DMSO, or aqueous mixtures of ethanol. The gelation efficiency of these glycolipid derivatives is dependent upon the structures of their acyl chains. In order to understand the influence of the anomeric position of the sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The synthesis and characterization of these novel analogs are reported.

SUBMITTER: Wang G

PROVIDER: S-EPMC3062983 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Simple Tyrosine Derivatives Act as Low Molecular Weight Organogelators.

Project description:The gelation of L-Tyr(tBu)-OH in tetrahydrofuran (THF) was discovered serendipitously. It was noted that this tremendously low molecular weight (LMW) compound has the ability to gel a wide variety of organic solvents (e.g., N,N-Dimetylformamide (DMF), THF, butanol, toluene), even in very low concentrations (i.e., 0.1 wt/v% in DMF). Addition of bases such as NaOH and piperidine enhanced the gel property. By changing the side-chain protecting group to tert-butyldimethylsilyl (TBDMS), a fluoride ion-responsive organogel was also acquired. This new organogelator responded fluoride ion concentration as low as 0.2 ppm. Characterization of microstructures and gel behaviours were studied by powder X-Ray diffraction spectroscopy (XRD), transmission electron microscopy (TEM), rheological measurements and molecular dynamics (MD) simulations. Experimental observations and theoretical simulations consistently show a fibre-like structure of the gel, in which the organogelator molecules are held together via a dense network of hydrogen bonds, and via van der Waals interactions between hydrophobic groups.

| S-EPMC6426947 | biostudies-literature

In situ formation of low molecular weight organogelators for slick solidification.

Project description:We have investigated the in situ formation of Low Molecular Weight Organogelator (LMWO) molecules in oil-on-water slicks through dual reactive precursor injection. This method alleviates the need for any carrier solvent or prior heating, therefore reducing the environmental impact of LMWOs, giving instantaneous gelation, even at low temperatures (-5 °C). We show minimal leaching from our gels into the water layer.

| S-EPMC9051380 | biostudies-literature

Protein-induced low molecular weight hydrogelator self-assembly through a self-sustaining process.

Project description:Controlling how, when and where a self-assembly process occurs is essential for the design of the next generation of smart materials. Along this route, enzyme-assisted self-assembly is a powerful tool developed during the last decade. Here we introduce another strategy allowing for spatiotemporal control over peptide self-assemblies. We use a Fmoc-peptide precursor in dynamic equilibrium with its low molecular weight hydrogelator (LMWH) through a reversible disulfide bond. In the absence of proteins, no self-assembly of the hydrogelator is observed. In the presence of proteins, their interactions with the precursor initiate a self-assembly process of the hydrogelator around them. This self-assembly displaces the equilibrium between precursor and LMWH according to Le Chatelier's principle, producing new hydrogelators available to pursue the self-assembly growth. One thus establishes a self-sustaining cycle fuelled by the self-assembly itself until full consumption of the LMWH. For proteins in solutions this process can lead to a supramolecular hydrogel whereas for proteins deposited on a surface, the gel growth is initiated exclusively from the surface.

| S-EPMC6509879 | biostudies-other

Self-Assembly of Low-Molecular-Weight Asymmetric Linear Triblock Terpolymers: How Low Can We Go?

Project description:The synthesis of two (2) novel triblock terpolymers of the ABC type and one (1) of the BAC type, where A, B and C are chemically different segments, such as polystyrene (PS), poly(butadiene) (PB1,4) and poly(dimethylsiloxane) (PDMS), is reported; moreover, their corresponding molecular and bulk characterizations were performed. Very low dimensions are evident from the characterization in bulk from transmission electron microscopy studies, verified by small-angle X-ray data, since sub-16 nm domains are evident in all three cases. The self-assembly results justify the assumptions that the high Flory-Huggins parameter, ?, even in low molecular weights, leads to significantly well-ordered structures, despite the complexity of the systems studied. Furthermore, it is the first time that a structure/properties relationship was studied for such systems in bulk, potentially leading to prominent applications in nanotechnology and nanopatterning, for as low as sub-10 nm thin-film manipulations.

| S-EPMC7728154 | biostudies-literature

Development of Low-Molecular-Mass Organogelators: Synthesis and Physical Properties of N-Linear Saturated Fatty Acyl-GABAs and Their Ester Derivatives.

Project description:We determined that compounds in which γ-aminobutyric acid (GABA) and linear saturated fatty acids of various lengths are amide-bonded, as found in the human brain, have the ability to gelate organic solvents. We also synthesized compounds of these GABA derivatives attached to 1,5-anhydro-d-glucitol (1,5-AG) or d-glucopyranose (Glc) via ester linkages, and these compounds were also found to be able to gelate organic solvents. From the comparative experiments of gelation using various lengths of N-linear saturated fatty acyl-GABAs and their ester derivatives, it was determined that the compound of N-tetradecanoic acyl-GABA bonded to 1,5-AG via ester linkage (C14GABA-AG) had a particularly high gel hardness and could gelate various organic solvents. Furthermore, field-emission scanning electron microscopy observations revealed the formation of a fibrous structure, which encapsulates the organic solvent and forms a gel. A variable-temperature Fourier transform infrared spectroscopy analysis revealed that the alkyl chains of N-linear saturated fatty acyl-GABAs are packed with an all-trans conformation, whereas the alkyl chains of the ester compounds attached to 1,5-AG or Glc are slightly skewed from the all-trans conformation due to the intermolecular hydrogen bonding of the amide groups. Here, we report the synthesis and analysis of N-linear saturated fatty acyl-GABA derivatives and the gelation mechanism.

| S-EPMC8374911 | biostudies-literature

A new family of urea-based low molecular-weight organogelators for environmental remediation: the influence of structure.

Project description:Gelation processes grant access to a wealth of soft materials with tailorable properties, in applications as diverse as environmental remediation, biomedicine and electronics. Several classes of self-assembling gelators have been studied and employ non-covalent bonds to direct assembly, but recently attention has come to focus on how the overall shape of the gelator molecule impacts its gelation. Here we study a new sub-family of low molecular weight organogelators and explore how steric rearrangement influences their gelation. The gels produced are characterised with X-ray diffraction and small-angle neutron scattering (SANS) to probe their ex situ and in situ gelation mechanisms. The best examples were then tested for environmental remediation applications, gelling petrol and oils in the presence of water and salts.

| S-EPMC6256360 | biostudies-literature

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properities.

Project description:This paper reports the self-assembly of two new tetrathiafulvalene (TTF) derivatives that contain one or two urethane groups. The formation of nanoribbons was evidenced by scanning electron microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T 1 was better than that of T 2 . The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV-vis and FTIR spectra were measured to explore noncovalent interactions. The driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and ?-? stacking interactions. The electronic conductivity of the T 1 and T 2 films was tested by a four-probe method.

| S-EPMC4685907 | biostudies-literature

Low-Molecular-Weight Organogelators Based on N-dodecanoyl-L-amino Acids-Energy Frameworks and Supramolecular Synthons.

Project description:Lauric acid was used to synthesize the low-molecular-weight organogelators (LMOGs), derivatives of two endogenous (L)-alanine, (L)-leucine, and three exogenous (L)-valine, (L)-phenylalanine, and (L)-proline amino acids. The nature of processes responsible for the gel formation both in polar and in apolar solvents of such compounds is still under investigation. Knowing that the organization of surfactant molecules affects the properties of nano scale materials and gels, we decided to elucidate this problem using crystallographic diffraction and energy frameworks analysis. The single crystals of the mentioned compounds were produced successfully from heptane/tBuOMe mixture. The compounds form lamellar self-assemblies in crystals. The energetic landscapes of single crystals of a series of studied amphiphilic gelators have been analyzed to explore the gelling properties. The presented results may be used as model systems to understand which supramolecular interactions observed in the solid state and what energy contributions are desired in the designing of new low-molecular-weight organic gelators.

| S-EPMC9867098 | biostudies-literature

Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs).

Project description:Phenylalanine functionalised norbornene (9:Na) functions as a potent, low molecular-mass (MW = 333 Da) ionic organogelator with a minimum gelating concentration of 0.5 wt% in THF, i-PrOH, 1,4-dioxane and n-BuOH. Fibrous crystals form in the gel and X-ray crystallography identified a cation mediated helical assembly process controlled by the chirality of the phenylalanine. In addition to excellent gelating properties 9:Na readily forms aqueous biphasic and triphasic systems.

| S-EPMC6001280 | biostudies-literature

Low Molecular Weight Norbornadiene Derivatives for Molecular Solar-Thermal Energy Storage.

Project description:Molecular solar-thermal energy storage systems are based on molecular switches that reversibly convert solar energy into chemical energy. Herein, we report the synthesis, characterization, and computational evaluation of a series of low molecular weight (193-260?g?mol(-1) ) norbornadiene-quadricyclane systems. The molecules feature cyano acceptor and ethynyl-substituted aromatic donor groups, leading to a good match with solar irradiation, quantitative photo-thermal conversion between the norbornadiene and quadricyclane, as well as high energy storage densities (396-629?kJ?kg(-1) ). The spectroscopic properties and energy storage capability have been further evaluated through density functional theory calculations, which indicate that the ethynyl moiety plays a critical role in obtaining the high oscillator strengths seen for these molecules.

| S-EPMC5096010 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data