Browse
Submit Data
Databases
API
Help

Dataset Information

51 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of self-curable polysulfone containing pendant benzoxazine units via CuAAC click chemistry.

ABSTRACT: Synthesis, characterization, and properties of new thermally curable polysulfone containing benzoxazine moieties in the side chain were investigated. First, chloromethylation and subsequent azidation processes were performed to form polysulfone containing pendant clickable azide groups. Independently, antagonist 3,4-dihydro-3-(prop-2-ynyl)-2H-benzoxazine was prepared by using paraformaldehyde, phenol and propargylamine. The following copper(I) catalyzed azide-alkyne cycloaddition click reaction was applied to obtain self-curable polysulfone with pendant benzoxazine units. The polymer and intermediates at various stages were characterized by 1H-NMR, 13C-NMR and FT-IR spectroscopies. The thermal properties and curing behavior of final polymer were investigated by differential scanning calorimetry and thermal gravimetric analysis. Compared to the neat polysulfone, the obtained polymers exhibited thermally more stable polymers.

SUBMITTER: Dizman C

PROVIDER: S-EPMC5812181 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of self-curable polysulfone containing pendant benzoxazine units via CuAAC click chemistry.

Dizman Cemil C Altinkok Cagatay C Tasdelen Mehmet Atilla MA

Designed monomers and polymers 20161121 1

Synthesis, characterization, and properties of new thermally curable polysulfone containing benzoxazine moieties in the side chain were investigated. First, chloromethylation and subsequent azidation processes were performed to form polysulfone containing pendant clickable azide groups. Independently, antagonist 3,4-dihydro-3-(prop-2-ynyl)-2H-benzoxazine was prepared by using paraformaldehyde, phenol and propargylamine. The following copper(I) catalyzed azide-alkyne cycloaddition click reaction ...[more]

PMID: 29491800

Similar Datasets

Peptide conjugation via CuAAC 'click' chemistry.

Project description:The copper (I)-catalyzed alkyne azide 1,3-dipolar cycloaddition (CuAAC) or 'click' reaction, is a highly versatile reaction that can be performed under a variety of reaction conditions including various solvents, a wide pH and temperature range, and using different copper sources, with or without additional ligands or reducing agents. This reaction is highly selective and can be performed in the presence of other functional moieties. The flexibility and selectivity has resulted in growing interest in the application of CuAAC in various fields. In this review, we briefly describe the importance of the structural folding of peptides and proteins and how the 1,4-disubstituted triazole product of the CuAAC reaction is a suitable isoster for an amide bond. However the major focus of the review is the application of this reaction to produce peptide conjugates for tagging and targeting purpose, linkers for multifunctional biomacromolecules, and reporter ions for peptide and protein analysis.

| S-EPMC6270195 | biostudies-literature

CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins.

Project description:In the context of discovering and quantifying terminal alkyne-based natural products, here we report the combination of CuAAC click chemistry with LC-MS for the detection of polyether toxins (prymnesins) associated with harmful algal blooms. The added-value of the CuAAC-based approach is evident from our ability to detect novel prymnesin-like compounds in algal species with previously uncharacterised toxins.

| S-EPMC6243676 | biostudies-literature

Biotin-Conjugated Cellulose Nanofibers Prepared via Copper-Catalyzed Alkyne-Azide Cycloaddition (CuAAC) "Click" Chemistry.

Project description:As potential high surface area for selective capture in diagnostic or filtration devices, biotin-cellulose nanofiber membranes were fabricated to demonstrate the potential for specific and bio-orthogonal attachment of biomolecules onto nanofiber surfaces. Cellulose acetate was electrospun and substituted with alkyne groups in either a one- or two-step process. The alkyne reaction, confirmed by FTIR and Raman spectroscopy, was dependent on solvent ratio, time, and temperature. The two-step process maximized alkyne substitution in 10/90 volume per volume ratio (v/v) water to isopropanol at 50 °C after 6 h compared to the one-step process in 80/20 (v/v) at 50 °C after 48 h. Azide-biotin conjugate "clicked" with the alkyne-cellulose via copper-catalyzed alkyne-azide cycloaddition (CuAAC). The biotin-cellulose membranes, characterized by FTIR, SEM, Energy Dispersive X-ray spectroscopy (EDX), and XPS, were used in proof-of-concept assays (HABA (4'-hydroxyazobenzene-2-carboxylic acid) colorimetric assay and fluorescently tagged streptavidin assay) where streptavidin selectively bound to the pendant biotin. The click reaction was specific to alkyne-azide coupling and dependent on pH, ratio of ascorbic acid to copper sulfate, and time. Copper (II) reduction to copper (I) was successful without ascorbic acid, increasing the viability of the click conjugation with biomolecules. The surface-available biotin was dependent on storage medium and time: Decreasing with immersion in water and increasing with storage in air.

| S-EPMC7353318 | biostudies-literature

[3+2] click chemistry approach to tetrazine containing polymers.

Project description:We report a [3+2] cycloaddition using 3,6-bis-propargyloxy-1,2,4,5-tetrazine and azides to synthesize energetic polymers containing 1,2,4,5-tetrazine within the scaffold. This work also includes [3+2] cycloaddition to crosslink azide containing glycidyl azide polymer (GAP). These reactions provide pathways for incorporation of 1,2,4,5-tetrazine into novel energetic materials using click-chemistry and provide an alternative polymer curing approach.

| S-EPMC9535468 | biostudies-literature

Click chemistry functionalization of self-assembling peptide hydrogels.

Project description:Self-assembling peptide (SAP) hydrogels provide a fibrous microenvironment to cells while also giving users control of biochemical and mechanical cues. Previously, biochemical cues were introduced by physically mixing them with SAPs prior to hydrogel assembly, or by incorporating them into the SAP sequence during peptide synthesis, which limited flexibility and increased costs. To circumvent these limitations, we developed "Click SAPs," a novel formulation that can be easily functionalized via click chemistry thiol-ene reaction. Due to its high cytocompatibility, the thiol-ene click reaction is currently used to crosslink and functionalize other types of polymeric hydrogels. In this study, we developed a click chemistry compatible SAP platform by addition of a modified lysine (lysine-alloc) to the SAP sequence, enabling effective coupling of thiol-containing molecules to the SAP hydrogel network. We demonstrate the flexibility of this approach by incorporating a fluorescent dye, a cellular adhesion peptide, and a matrix metalloproteinase-sensitive biosensor using the thiol-ene reaction in 3D Click SAPs. Using atomic force microscopy, we demonstrate that Click SAPs retain the ability to self-assemble into fibers, similar to previous systems. Additionally, a range of physiologically relevant stiffnesses can be achieved by adjusting SAP concentration. Encapsulated cells maintain high viability in Click SAPs and can interact with adhesion peptides and a matrix metalloproteinase biosensor, demonstrating that incorporated molecules retain their biological activity. The Click SAP platform supports easier functionalization with a wider array of bioactive molecules and enables new investigations with temporal and spatial control of the cellular microenvironment.

| S-EPMC10092743 | biostudies-literature

A synthetic approach to 'click' neoglycoprotein analogues of EPO employing one-pot native chemical ligation and CuAAC chemistry.

Project description:The clinical significance of batch-wise variability on the pharmacokinetics and potency of commercial erythropoietin (EPO), prepared recombinantly as a heterogeneous mixture of glycoforms, necessitates the development of synthetic strategies to afford homogenous EPO formulations. Herein we present a previously unexplored and divergent route towards 'click' neoglycoprotein analogues of EPO, employing one-pot native chemical ligation (NCL) of alkynylated peptides and copper-catalysed azide-alkyne cycloaddition (CuAAC) with azido monosaccharides. By design, our synthetic platform permits glycosylation at virtually any stage, providing flexibility for the synthesis of various glycoforms for biological analysis. Insights obtained from attempted folding of our 'click' neoglycoprotein EPO analogue, bearing four different neutral sugar moieties, highlight the important role played by the charged oligosaccharides present in native EPO glycoproteins.

| S-EPMC6345360 | biostudies-literature

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy.

Project description:A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20-55%. This strategy allows the construction of six heterocycles in two stages of the reaction.

| S-EPMC7696539 | biostudies-literature

First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC.

Project description:A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities.

| S-EPMC7570757 | biostudies-literature

Synthesis of β-cyclodextrin containing copolymer via "click" chemistry and its self-assembly in the presence of guest compounds.

Project description:We report the synthesis of a hydrophilic copolymer with one polyethylene glycol (PEG) block and one β-cyclodextrin (β-CD) containing block by a "click" reaction between azido-substituted β-CD and propargyl flanking copolymer. (1)H NMR study suggested a highly efficient conjugation of β-CD units by this approach. The obtained copolymer was used as a host macromolecule to construct assemblies in the presence of hydrophobic guests. For assemblies containing a hydrophobic polymer, their size can be simply adjusted by simply changing the content of hydrophobic component. By serving as a guest molecule, hydrophobic drugs can also be loaded accompanying the formation of nanoparticles, and the drug payload is releasable. Therefore, the copolymer synthesized herein can be employed as a carrier for drug delivery.

| S-EPMC3893059 | biostudies-literature

Polymeric Micellar Nanocatalysts for CuAAC Click Reaction in Water.

Project description:Polymer-supported copper catalysts have attained a prominent status and continue to be a focal point of ongoing research and development due to their adaptable properties, which make them invaluable tools for diverse catalytic reactions in aqueous solutions. The objective of this investigation is to develop catalysts supported on a random copolymer that can be assembled in water. A series of random copolymer was prepared through postpolymerization modification of a polymer precursor, poly(pentafluorophenyl acrylate) (PPFPA), employing 1-amino-2-propanol and 1-(3-aminopropyl)imidazole via nucleophilic substitution. Following alkylation and copper insertion, it yielded a polymer-supported copper (Cu) catalyst on poly(N-(2-hydroxypropyl)acrylamide)-ran-poly(N-(3-(1-benzylimidazolium-3-yl)propyl)acrylamide) PHPAM76-ran-PILAM24(Cu(I)), capable of assembling into micellar catalysts in water with a diameter of 175 nm and low polydispersity. These developed self-assembled micelles can serve as nanocatalysts for the copper-catalyzed azide-alkyne cycloaddition (CuAAC) between alkyne and azide derivatives in an aqueous system. Employing PHPAM76-ran-PILAM24(Cu(I)) as the micellar catalyst with a 1 mol % Cu loading significantly enhances reaction yields (95-99%), achieving complete conversion at room temperature within 1-4 h, with minimal copper residue detected in the product (<0.06 ppm) after a straightforward extraction process. This research highlights the versatility of postpolymerization modification of the polymer precursor, PPFPA through nucleophilic substitution as a promising strategy for the development of tailored nanocatalysts for diverse chemical reactions in the future.

| S-EPMC11924335 | 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