Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Exploiting 1,2,3-Triazolium Ionic Liquids for Synthesis of Tryptanthrin and Chemoselective Extraction of Copper(II) Ions and Histidine-Containing Peptides.

ABSTRACT: Based on a common structural core of 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine, a number of bicyclic triazolium ionic liquids 1-3 were designed and successfully prepared. In our hands, this optimized synthesis of ionic liquids 1 and 2 requires no chromatographic separation. Also in this work, ionic liquids 1, 2 were shown to be efficient ionic solvents for fast synthesis of tryptanthrin natural product. Furthermore, a new affinity ionic liquid 3 was tailor-synthesized and displayed its effectiveness in chemoselective extraction of both Cu(II) ions and, for the first time, histidine-containing peptides.

SUBMITTER: Li HY

PROVIDER: S-EPMC6274210 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Exploiting 1,2,3-Triazolium Ionic Liquids for Synthesis of Tryptanthrin and Chemoselective Extraction of Copper(II) Ions and Histidine-Containing Peptides.

Li Hsin-Yi HY Chen Chien-Yuan CY Cheng Hui-Ting HT Chu Yen-Ho YH

Molecules (Basel, Switzerland) 20161013 10

Based on a common structural core of 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine, a number of bicyclic triazolium ionic liquids 1-3 were designed and successfully prepared. In our hands, this optimized synthesis of ionic liquids 1 and 2 requires no chromatographic separation. Also in this work, ionic liquids 1, 2 were shown to be efficient ionic solvents for fast synthesis of tryptanthrin natural product. Furthermore, a new affinity ionic liq ...[more]

PMID: 27754392

Similar Datasets

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions.

Project description:We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant ?-? stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-% cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs.

| S-EPMC7435399 | biostudies-literature

Combinatorial discovery of small-molecule 1,2,3-triazolium ionic liquids exhibiting lower critical solution temperature phase transition.

Project description:Both lower and upper critical solution temperature (LCST and UCST) systems are two typical phase behaviors of thermoresponsive materials with solvents, in which LCST is far less common than UCST. Recent studies on ionic liquids carrying LCST phase transitions have predominantly focused on quaternary ammonium- and phosphonium-based ionic salts. Based on the 1,2,3-triazole core structure assemblable by azide-alkyne cycloaddition click reaction, this work reports the combinatorial synthesis of 1,3,4-trialkylated 1,2,3-triazolium ionic liquids in three libraries with a total of 160 ionic liquids and demonstrates, for the first time, their values in temperature-switchable phase transition with water. In this work, the successful discovery of a new thermoresponsive ionic liquid b26, based on the structure-and-phase separation study of b8 and b9, perfectly exemplified the true value of the tunability of ionic liquid fine structures. For all 160 ionic liquids synthesized, 155 are liquid at room temperature and 22 room-temperature ionic liquids were found to exhibit thermoresponsive phase transitions having low Tc values in water. To the best of our knowledge, this comprehensive study is the first report of small-molecule 1,2,3-triazolium ionic liquids that exhibit LCST property in water.

| S-EPMC7589527 | biostudies-literature

BILFF: All-Atom Force Field for Modeling Triazolium- and Benzoate-Based Ionic Liquids.

Project description:We present an extension of our previously developed all-atom force field BILFF (Bio-polymers in Ionic Liquids Force Field) to three different ionic liquids: 1-ethyl-3-methyl-1,2,3-triazolium acetate ([EMTr][OAc]), 1-ethyl-3-methyl-1,2,3-triazolium benzoate ([EMTr][OBz]), and 1-ethyl-3-methylimidazolium benzoate ([EMIm][OBz]). These ionic liquids are of practical importance as they have the ability to dissolve significant amounts of cellulose even at room temperature. Our force field is optimized to accurately reproduce the strong hydrogen bonding in the system with nearly quantum chemical accuracy. A very good agreement between the microstructure of the quantum chemical simulations over a wide temperature range and experimental density data with the results of BILFF were observed. Non-trivial effects, such as the solvation shell structure and π-π stacking of the cations, are also accurately reproduced. Our force field enables accurate simulations of larger systems, such as solvated cellulose in different (aqueous) ionic liquids, and is the first to present the optimized parameters for mixtures of these solvents and water.

| S-EPMC10674667 | biostudies-literature

Design of Clickable Ionic Liquid Monomers to Enhance Ionic Conductivity for Main-Chain 1,2,3-Triazolium-Based Poly(Ionic Liquid)s.

Project description:A series of clickable α-azide-ω-alkyne ionic liquid (IL) monomers with an ethylene oxide spacer were developed and applied to the synthesis of 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) with high ionic conductivities via one-step thermal azide-alkyne cycloaddition click chemistry. Subsequently, the number of IL moieties in the resultant TPILs was further increased by N-alkylation of the 1,2,3-triazole-based backbones of the TPILs with a quarternizing reagent. This strategy affords the preparation of TPILs having either one or two 1,2,3-triazolium cations with bis(trifluoromethylsulfonyl)imide anions in a monomer unit. Synthesis of the TPILs was confirmed by 1H and 13C NMR spectroscopy and gel permeation chromatography. The effects of the length of the ethylene oxide spacer and the number of IL moieties in the IL monomer unit on the physicochemical properties of the TPILs were characterized by differential scanning calorimetry, thermogravimetric analysis, and impedance spectroscopy. The introduction of a longer ethylene oxide spacer or an increase in the number of IL moieties in the monomer unit resulted in TPILs with lower glass-transition temperatures and higher ionic conductivities. The highest ionic conductivity achieved in this study was 2.0 × 10-5 S cm-1 at 30 °C. These results suggest that the design of the IL monomer provides the resultant polymer with high chain flexibility and a high IL density, and so it is effective for preparing TPILs with high ionic conductivities.

| S-EPMC8153667 | biostudies-literature

Significant enhanced uranyl ions extraction efficiency with phosphoramidate-functionalized ionic liquids via synergistic effect of coordination and hydrogen bond.

Project description:The influence of the linking group between the phosphoryl and bridging moieties in phosphoryl-containing task-specific ionic liquids (TSILs) on the extraction of uranyl ions was experimentally and theoretically investigated. A novel phosphoramidate-based TSIL with an amine group as the linking moiety resulted in a higher uranyl ion extraction efficiency compared with that of other phosphoryl-based TSILs. A distribution ratio of 4999?±?51 can be achieved for uranyl ions. The uranyl ions (76.7?±?1.5%) were stripped from the loaded ionic liquid phase in a single stage using 0.05?M diethylenetriamine pentaacetic acid in a 1.0?M guanidine carbonate solution. The extraction stoichiometry of the uranyl ions was determined by a slope analysis of the extraction data. Furthermore, the fundamental nature of the interaction between the phosphoramidate-based TSIL and uranyl ions was theoretically studied for the first time. The theoretical calculations demonstrated that the synergistic effect of the complexation interaction and H-bond formation between the phosphoramidate-functional ionic liquid and uranyl nitrate led to the higher extraction efficiency. These results provide a basis for rational design, synthesis and potential applications of novel TSILs for uranyl extraction.

| S-EPMC5691085 | biostudies-literature

Antimicrobial 1,3,4-trisubstituted-1,2,3-triazolium salts.

Project description:A series of 1,3,4-trisubstituted-1,2,3-triazolium bromide salts were prepared by efficient two-step sequences of azide-alkyne cycloaddition and benzylic substitution. The antimicrobial activity of each triazolium salt and correlating triazole precursor was evaluated using a minimum inhibitory concentration (MIC) assay. MIC activities as low as 1?µM against Gram-positive bacteria, 8?µM against Gram-negative bacteria and 4?µM against fungi were observed for salt analogs, while neutral triazoles were inactive. Analogs representing selective and broad-spectrum antimicrobial activity were each identified. MIC structure-activity relationships observed within this motif indicate that the presence of cationic charge and balance of overall hydrophobicity are strongly impactful, while benzyl vs. aryl substituent identity and variation of substituent regiochemistry are not.

| S-EPMC6214158 | biostudies-literature

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(?-hydroxypropyl)imidazolium- and triazolium-based ionic liquids.

Project description:Racemic 1-(?-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.

| S-EPMC3628848 | biostudies-literature

Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction.

Project description:New 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excellent chemical yields (up to 90%) and high selectivities (up to 94% ee). The progress of the reactions could be monitored by TLC and NMR, and the ionic liquid-supported chiral auxiliaries could be recovered by simple extraction.

| S-EPMC6766834 | biostudies-other

Magnetic Ionic Liquids as Solvents for RNA Extraction and Preservation.

Project description:Ribonucleic acid (RNA) is particularly sensitive to enzymatic degradation by endonucleases prior to sample analysis. In-field preservation has been a challenge for RNA sample preparation. Very recently, hydrophobic magnetic ionic liquids (MIL) have shown significant promise in the area of RNA extraction. In this study, MILs were synthesized and employed as solvents for the extraction and preservation of RNA in aqueous solution. RNA samples obtained from yeast cells were extracted and preserved by the trihexyl(tetradecyl) phosphonium tris(hexafluoroacetylaceto)cobaltate(II) ([P66614 +][Co(hfacac)3 -]) and trihexyl(tetradecyl) phosphonium tris(phenyltrifluoroacetylaceto)cobaltate(II) ([P66614 +][Co(Phtfacac)3 -]) MIL with a dispersion of the supporting media, polypropylene glycol, at room temperature for up to a 7 and 15 day period, respectively. High-quality RNA treated with ribonuclease A (RNase A) was recovered from the tetra(1-octylimidazole)cobaltate(II) di(l-glutamate) ([Co(OIM)4 2+][Glu-]2) and tetra(1-octylimidazole)cobaltate(II) di(l-aspartate) ([Co(OIM)4 2+][Asp-]2) MILs after a 24 h period at room temperature. Quantitative reverse transcription polymerase chain reaction (qRT-PCR) and agarose gel electrophoresis were used to determine the effect of RNA preservation. Furthermore, the preservation mechanism was investigated by exploring the partitioning of RNase A into the MIL using high-performance liquid chromatography.

| S-EPMC7241037 | biostudies-literature

Protic Ionic Liquids for Lignin Extraction-A Lignin Characterization Study.

Project description:Protic ionic liquids (PILs) have been established as effective solvents for the selective extraction and recovery of lignin from lignocellulosic biomass. In this study, we utilize extensive analytical techniques to characterize the PIL-extracted lignins to (1) expand on the physical/chemical structure, and to (2) develop a better understanding of the mechanism behind the lignin dissolution process. The PIL-lignins were characterized using elemental and FT-IR analyses, alongside molecular weight distribution and chemical modeling via MM2. For the more ionic pyrrolidinium acetate ([Pyrr][Ac]), there is an increase in the fragmentation of lignin, resulting in lignin with a smaller average molecular weight and a more uniform dispersity. This lends better understanding to previous findings indicating that higher ionicity in a PIL leads to increased lignin extraction.

| S-EPMC5855650 | 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