Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Bronsted acids.

ABSTRACT: The effective and efficient removal of the BF2 moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion in near-quantitative yields. Compared to existing methods, these conditions are relatively mild and operationally simple, requiring only reaction at room temperature for six hours (TFA) or overnight (HCl).

SUBMITTER: Yu M

PROVIDER: S-EPMC4311716 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids.

Yu Mingfeng M Wong Joseph K-H JK Tang Cyril C Turner Peter P Todd Matthew H MH Rutledge Peter J PJ

Beilstein journal of organic chemistry 20150109

The effective and efficient removal of the BF2 moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion in near-quantitative yields. Compared to existing methods, these conditions are relatively mild and operationally simple, requiring only reaction at room temperature for six hours (TFA) or overnight (H ...[more]

PMID: 25670990

Similar Datasets

Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Bronsted acid cocatalyst.

Project description:The Ir-catalyzed highly efficient asymmetric hydrogenation of benzoxazinones and derivatives was successfully developed with N-methylated ZhaoPhos L5 as the ligand, which may display a new activation mode with a single anion-binding interaction among the substrate, cocatalyst Brønsted acid and ligand. This synthetic approach afforded a series of chiral dihydrobenzoxazinones and derivatives with excellent results (>99% conversion, 88-96% yields, 91->99% ee, up to 40 500 TON). A key to success is the utilization of a strong Brønsted acid as the cocatalyst, such as hydrochloric acid, to form a possible single anion-binding interaction with the substrate and catalyst, which greatly contributed to the improvement of reactivity and enantioselectivity. Importantly, a creative and efficient synthetic route was developed to construct the important intermediate for the potential IgE/IgG receptor modulator through our catalytic methodology system.

| S-EPMC6471538 | biostudies-literature

Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.

Project description:A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials.

| S-EPMC6693341 | biostudies-literature

Synthesis of N-Substituted 3-Amino-4-halopyridines: A Sequential Boc-Removal/Reductive Amination Mediated by Bronsted and Lewis Acids.

Project description:N-Substituted 3-amino-4-halopyridines are valuable synthetic intermediates, as they readily provide access to imidazopyridines and similar heterocyclic systems. The direct synthesis of N-substituted 3-amino-4-halopyridines is problematic, as reductive aminations and base-promoted alkylations are difficult in these systems. A high yielding deprotection/alkylation protocol mediated by trifluoroacetic acid and trimethylsilyl trifluoromethanesulfonate is described, providing access to a wide scope of N-substituted 3-amino-4-halopyridines. This protocol furnishes many reaction products in high purity without chromatography. Similar reductive amination conditions were also established for deactivated anilines.

| S-EPMC5835363 | biostudies-literature

Curcuminoid-BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage.

Project description:Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine.

| S-EPMC5669223 | biostudies-literature

Thioester deprotection using a biomimetic NCL approach

Project description:The reversibility of the thiol-thioester linkage has been broadly employed in many fields of biochemistry (lipid synthesis) and chemistry (dynamic combinatorial chemistry and material science). When the transthioesterification is followed by a S-to-N acyl transfer to give an amide bond, it is called Native Chemical Ligation (NCL), a high-yield chemoselective process used for peptide synthesis. Recently, we described thioglycolic acid (TGA) as a useful reagent for thioester deprotection both in solution and anchored to a solid-support under mild conditions. Inspired by NCL, in this work, we extended this approach and explored the use of 2-aminothiols for the deprotection of thiols bearing an acyl group. The best results were obtained using cysteamine or L-cysteine in an aqueous buffer pH 8 at room temperature for 30 min. The described approach was useful for S-acetyl, S-butyryl, and S-benzoyl heterocycles deprotection with yields up to 84%. Employing this methodology, we prepared six new analogs 2 of mercaptomethyl bisthiazolidine 1, a useful inhibitor of a wide-range of Metallo-β-Lactamases (MBLs). Compared with the previous methodologies (TGA polymer supported and TGA in solution), the biomimetic deprotection herein described presents better performance with higher yields, shorter reaction times, less time-consuming operations, easier setup, and lower costs.

| S-EPMC9441695 | biostudies-literature

Kinetic Studies on the Conversion of Levoglucosan to Glucose in Water Using Bronsted Acids as the Catalysts.

Project description:Fast pyrolysis is as a promising and versatile technology to depolymerize and concentrate sugars from lignocellulosic biomass. The pyrolysis liquids produced contain considerable amounts of levoglucosan (1,6-anhydro-β-d-glucopyranose), which is an interesting source for glucose (GLC). Here, we report a kinetic study on the conversion of levoglucosan (LG) to GLC in water using sulfuric and acetic acid as the catalysts under a wide range of conditions in a batch setup. The effects of the initial LG loading (0.1-1 M), sulfuric and acetic acid concentrations (0.05-0.5 M and 0.5-1 M, respectively), and reaction temperatures (80-200 °C) were determined. Highest GLC yields were obtained using sulfuric acid (98 mol %), whereas the yields were lower for acetic acid (maximum 90 mol %) due to the formation of byproducts such as insoluble polymers (humins). The experimental data were modeled using MATLAB software, and relevant kinetic parameters were determined. Good agreement between experimental and model was obtained when assuming that the reaction is first order with respect to LG. The activation energies were 123.4 kJ mol-1 and 120.9 kJ mol-1 for sulfuric and acetic acid, respectively.

| S-EPMC5997467 | biostudies-literature

Efficient protein depletion by genetically controlled deprotection of a dormant N-degron.

Project description:Methods that allow for the manipulation of genes or their products have been highly fruitful for biomedical research. Here, we describe a method that allows the control of protein abundance by a genetically encoded regulatory system. We developed a dormant N-degron that can be attached to the N-terminus of a protein of interest. Upon expression of a site-specific protease, the dormant N-degron becomes deprotected. The N-degron then targets itself and the attached protein for rapid proteasomal degradation through the N-end rule pathway. We use an optimized tobacco etch virus (TEV) protease variant combined with selective target binding to achieve complete and rapid deprotection of the N-degron-tagged proteins. This method, termed TEV protease induced protein inactivation (TIPI) of TIPI-degron (TDeg) modified target proteins is fast, reversible, and applicable to a broad range of proteins. TIPI of yeast proteins essential for vegetative growth causes phenotypes that are close to deletion mutants. The features of the TIPI system make it a versatile tool to study protein function in eukaryotes and to create new modules for synthetic or systems biology.

| S-EPMC2683728 | biostudies-literature

Facile deprotection of F-BODIPYs using methylboronic acid.

Project description:4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) are deprotected through removal of the -BF2 moiety upon treatment with methylboronic acid. The tolerance of various substitution patterns about the dipyrrinato core is demonstrated via the deprotection of thirteen F-BODIPYs and an F-aza-BODIPY. Work-up with aq. HBr affords the desired dipyrin HBr salt in quantitative yield without need for purification.

| S-EPMC9055154 | biostudies-literature

Urazolium diacetate as a new, efficient and reusable Bronsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones.

Project description:Urazolium diacetate catalyzed synthesis of new derivatives of 1,3-thiazolidine-4-ones (azo dispersive dyes family) via multicomponent reaction of various aldehydes, thioglycolic acid and 4-aminoazobenzene under solvent-free reaction was reported. This avenue for the synthesis of new derivatives of thiazolidine-4-one has advantages as: short reaction times, high yields, green aspect of chemistry and environmental friendliness, easy workup, solvent-free conditions and convenient operation.

| S-EPMC9047527 | biostudies-literature

Hydroxyethyl-Modified Cycloheptatriene-BODIPY Derivatives as Specific Tau Imaging Probes.

Project description:Near-infrared fluorescence (NIRF) imaging as an exquisite sensitive, high spatial-resolution, and real-time tool plays an important role in visualizing pathologies in the brain. In this study, we designed and synthesized a series of NIR probes of hydroxyethyl cycloheptatriene-BODIPY derivatives that have demonstrated strong binding specificity to native neurofibrillary tangles (NFTs) in Alzheimer's disease (AD) brain sections. The improved hydrophilicity of TNIR7-9 and TNIR7-11 resulted in faster clearance rates from healthy brains (4.2 and 10.9, respectively) compared to previously reported compounds. Furthermore, TNIR7-13, which features a fluorinated modification, exhibited a high binding affinity to Tau aggregates (Kd = 11.8 nM) and held promise for future PET studies.

| S-EPMC10424304 | 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