Glutamide

A general strategy to tune the achiral main chain polymers into helical nanoassemblies was proposed based on the co-gelation approach. As an example, two achiral main chain polymers, PCz8 and PSi8, were selected, and their co-assembly with an amphiphilic l- or d-glutamide gelator was investigated. Although the polymers could not form gels individually, they could form co-gels with the gelator and the resultant gels exhibited macroscopic supramolecular chirality, which could be confirmed by CD spectra and SEM observations...

A double β-alanylated L-glutamide-derived organic phase has been newly designed and synthesized in such a way that integrated H-bonding (interaction) sites make it very suitable for the separation of versatile analytes, including shape-constrained isomers, and nonpolar, polar and basic compounds. The β-alanine residues introduced into two long-chain alkyl group moieties provide ordered polar groups through H-bonding among the amide groups.

We have reported that self-assembling glutamide lipid-grafted porous silica particles show high selectivity towards polycyclic aromatic hydrocarbons (PAHs) and bio-molecules. This enhancement of molecular recognition is brought about by the formation of a highly ordered structure in the glutamide lipid through intermolecular hydrogen bonding. To utilise, for selective separations, the highly oriented structure of glutamide lipids on the silica surface, in this study, we synthesised four glutamide lipids with different substitution groups and studied the separation behaviours of the glutamide lipid-grafted porous silica particles as reversed phase high-performance liquid chromatography (RP-HPLC) stationary phases...

Self-assembled chiral nanostructures such as nanofibers and nanotubes formed by a pyridylpyrazole-conjugated l-glutamide showed an enantioselective recognition toward a fluorescence labeled chiral amino acid.

Chiral nanostructure, such as the double helix of DNA and α-helix of protein, plays an important role in biochemistry and material sciences. In the organism system, the biological entities always exhibit homochirality and show preference toward one specific enantiomer. How the opposite enantiomers will affect the chirality of the supramolecular nanostructures and their interactions with the biological molecules remains an important issue. In this study, two gelators bearing amphiphilic l-glutamide and d- or l-pantolactone (abbreviated as DPLG and LPLG) were designed, and their self-assembly behavior and interactions with proteins were investigated...

Although solvent is the major component of the gel, it still remains unclear how the solvent molecules take part in the formation of the gel nanostructures in many gels. In this study it was observed that the vicinal effect on gel formation as well as their nanostructures, that is, the vicinal solvent molecules to the gelator, determine the molecular packing and their subsequent structures and properties. A naphthylacryl-conjugated L-glutamide gelator was found to form organogels in various solvents and nanofiber structures...

A series of new π-conjugated gelators that contain various aromatic rings (phenyl, naphthyl, 9-anthryl) and amphiphilic L-glutamide was designed, and their gel formation in organic solvents and self-assembled nanostructures was investigated. The gelators showed good gelation ability in various organic solvents that ranged from polar to nonpolar. Those gelator molecules with small rings such as phenyl and naphthyl self-assembled into nanotube structures in most organic solvents and showed strong blue emission...

Novel amphiphilic molecules composed of naphthylacryl and L-glutamide moieties (1-NA and 2-NA) have been designed and their organogel formation in various organic solvents as well as their self-assembled nanostructures have been investigated. Both compounds formed organogels in many organic solvents, ranging from nonpolar to polar, and self-assembled into essentially nanofiber structures, although some twist or belt structures could be observed in certain solvents. A gel of compound 2-NA in ethanol initially self-assembled into nanofibers and then these were transformed into a family of coaxial hollow toruloid-like (CHTL) nanostructures under irradiation, in which various toroids and disks of different sizes were stacked coaxially...

BACKGROUND: To investigate the effect of microbiological and immunological enteral nutrition (MEIN composed by probiotics, L-Glutamide, deep-sea fish oil and Nutrison Fibre) on intestinal function and immune status in the patients with long-term use of antibiotics. PATIENTS AND METHODS: 56 severe apoplexy patients with pulmonary infectious complication were randomly divided into two groups: a microbiological and immunological enteral nutrition group (MEIN group, n=28) and an enteral nutrition group (EN group, n=28)...

The self-assembly of a low-molecular-weight organogelator into various hierarchical structures has been achieved for a pyridylpyrazole linked L-glutamide amphiphile in different solvents. Upon gel formation, supramolecular chirality was observed, which exhibited an obvious dependence on the polarity of the solvent. Positive supramolecular chirality was obtained in nonpolar solvents, whereas it was inverted into negative supramolecular chirality in polar solvents. Moreover, the gelator molecules self-assembled into a diverse array of nanostructures over a wide scale range, from nanofibers to nanotubes and microtubes, depending on the solvent polarity...

Three metal complexes consisting of Li(+), Zn(2+), and Al(3+) and quinolinol-functionalized L-glutamides (HQLG), (abbreviated as LiHQLG, Zn(HQLG)2, and Al(HQLG)3) were found to form fluorescent metallogels in several organic solvents. In solution, these chiral complexes showed neither any CD signal in the chromophore region nor chiral recognition of the chiral species. However, upon gel formation, the supramolecular chirality emerged because of the self-assembled nanostructures, which provided an opportunity for the chiral recognition of enantiomeric ligands...

A dual-functional metallogel, which was based on the copper(II) complex of quinolinol-substituted L-glutamide, showed both redox-responsive and enantioselective properties; moreover, the metallogels collapsed into a sol after reduction and could be revived upon subsequent oxidation. The supramolecular chirality and morphology also reversible changed with the gel-sol transition. Furthermore, the metallogels showed new enantioselective recognition towards chiral aromatic amino acids. A new emission band in the blue-light region at around 393 nm appeared when the metallogels encountered L-aromatic amino acids, whereas no new emission band was observed for the corresponding D-aromatic amino acids...

A glutamide gelator, 1, was synthesized, and a weak emission enhancement was observed during its gelation. In addition, 1 could be an excellent scaffold for successfully embedding an energy acceptor, 2, into its aggregate to obtain highly efficient energy transfer. An amplification of the emission enhancement was observed in the two-component gels compared to that of the neat gel of 1 during gel formation. For example, 1 induced only a 2.5-fold increase in emission intensity, whereas a 23-fold enhanced emission could be observed in the two-component gel with only 1...

The relationship between molecular gel-forming compound-based double-alkylated L-glutamide-derived functional group-integrated organic phase (Sil-FIP) structure and chromatographic performance is investigated and compared with widely used alkyl phases (C(30), polymeric and monomeric C(18)) as references. The functional group-integrated molecular gel on silica is chemically designed newly in a way that the weak interaction sites are integrated with high orientation and high selectivity can be realized by multiple interactions with the solutes...

A newly designed terephthalic acid substituted amphiphilic L-glutamide was found to form organogels in DMSO and a broad range of metal ions, from simple Na(+), Li(+) to Cu(2+), Ni(2+), Eu(3+) and Tb(3+), could turn the self-assembled nanostructure into a uniform helical twist.

A novel alternating copolymer-based organic phase was synthesized using a new N-substituted maleimide monomer for the development of alternating copolymer-grafted silica for high-performance liquid chromatographic applications. This new monomer (DGMI) was copolymerized with octadecyl acrylate (ODA) from 3-mercaptopropyltrimethoxysilane-grafted silica to produce Sil-poly(ODA-alt-DGMI). The organic phase was characterized by the elemental analysis and the diffuse reflectance infrared Fourier transform spectroscopy...

We describe the synthesis of metal chelating polymers based on polyaspartamide and polyglutamide backbones as carriers for (111)In in radioimmunoconjugates. These polymers [PAsp(DTPA), PGlu(DTPA)] have a biotin end group and diethylenetriaminepentaacetic acid (DTPA) chelators attached to the primary amines of the diethylenetriamine (DET) pendant groups of biotin-poly{N'-[N-(2-aminoethyl)-2-aminoethyl]aspartamide} [PAsp(DET)] and of biotin-poly{N'-[N-(2-aminoethyl)-2-aminoethyl]glutamide} [PGlu(DET)]. Like Asn-containing proteins and polypeptides, polyaspartamides undergo uncatalyzed degradation under model physiological conditions (10 mM phosphate buffer, pH 7...

New amphiphilic gelators that contained both Schiff base and L-glutamide moieties, abbreviated as o-SLG and p-SLG, were synthesized and their self-assembly in various organic solvents in the absence and presence of metal ions was investigated. Gelation test revealed that o-SLG formed a thermotropic gel in many organic solvents, whilst p-SLG did not. When metal ions, such as Cu(2+), Zn(2+), Mg(2+), Ni(2+), were added, different behaviors were observed. The addition of Cu(2+) induced p-SLG to from an organogel...

In the design of new cationic lipids for gene transfection, the chemistry of linkers is widely investigated from the viewpoint of biodegradation and less from their contribution to the biophysical properties. We synthesized two dodecyl lipids with glutamide as the backbone and two lysines to provide the cationic headgroup. Lipid 1 differs from Lipid 2 by the presence of an amide linkage instead of an ester linkage that characterizes Lipid 2. The transfection efficiency of lipoplexes with cholesterol as colipid was found to be very high with Lipid 1 on Chinese Hamster Ovary (CHO) and HepG2 cell lines, whereas Lipid 2 has shown partial transfection efficiency on HepG2 cells...

A new ex-TTF-based organogelator with L-glutamide-derived lipid unit (compound 1) was synthesized and characterized. The resulting transparent organogels can be obtained with several organic solvents such as toluene, DMSO, and ethanol. It is interesting that its gelation ability can be further enhanced by addition of C(60). The (1)H NMR and absorption spectral studies indicate that the intermolecular interaction between the ex-TTF unit in 1 and C(60) may be responsible for this phenomenon. Further studies imply that the assembly structures in the gel phases in the absence and presence of C(60) may be different...