There has been considerable interest in pan-assay interference (PAINS)58 (link) SMARTS patterns recently. We used the Rdkit version53 of the Guha translation57 of the original 480 PAINS expressed in Sybyl Line Notation (SLN).58 (link) All molecules in ZINC have been annotated and are searchable by PAINS and other SMARTS patterns. We compute a reactivity molecular property from the pattern membership of each molecule. The reactivity categories are A) anodyne; 1) clean (PAINS-ok); 2) mild (weakly reactive, typically as a nucleophile or electrophile); 3) reactive; 4) unstable or irrelevant for screening. For #4 we do not build molecular models for non-covalent docking (e.g. boronic acids). We also curated 40 patterns used by the prior version of ZINC. SMARTS patterns are rendered using SMARTSViewer.110 (link)
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Boronic Acids
Boronic Acids
Boronic acids are organoboron compounds containing the functional group -B(OH)2.
They are widely used in organic synthesis, particularly in Suzuki cross-coupling reactions and other boron-based transformations.
Boronic acids exhibit unique properties, such as the ability to form cyclic esters with diols and to interact with various nucleophiles.
This versatile class of compounds finds applications in medicinal chemistry, materials science, and biochemistry.
Researchers can explore the latest protocols and methods for working with boronic acids using AI-driven platforms like PubCompare.ai, which help identify the most reproducible and accurate appraoches from published literature, preprints, and patents.
They are widely used in organic synthesis, particularly in Suzuki cross-coupling reactions and other boron-based transformations.
Boronic acids exhibit unique properties, such as the ability to form cyclic esters with diols and to interact with various nucleophiles.
This versatile class of compounds finds applications in medicinal chemistry, materials science, and biochemistry.
Researchers can explore the latest protocols and methods for working with boronic acids using AI-driven platforms like PubCompare.ai, which help identify the most reproducible and accurate appraoches from published literature, preprints, and patents.
Most cited protocols related to «Boronic Acids»
Analgesics
Biological Assay
Boronic Acids
Pain
Zinc
Acids
Benzene
Boronic Acids
Carbon-13 Magnetic Resonance Spectroscopy
diphenyl
Esters
Fingers
Gas Chromatography-Mass Spectrometry
Mass Spectrometry
Nexus
NMR, Multinuclear
Palladium
Phenols
Polychlorinated Biphenyls
Spectrometry, Mass, Electrospray Ionization
tetramethylsilane
triphenylphosphine
Workers
There has been considerable
interest in pan-assay interference (PAINS)58 (link) SMARTS patterns recently. We used the RDKit version53 of the Guha translation57 (link) of
the original 480 PAINS expressed in Sybyl Line Notation (SLN).58 (link) All molecules in ZINC have been annotated and
are searchable by PAINS and other SMARTS patterns. We compute a reactivity molecular property from the pattern membership
of each molecule. The reactivity categories are A) anodyne; B) clean
(PAINS-ok); C) mild (weakly reactive, typically as a nucleophile or
electrophile); D) reactive; E) unstable or irrelevant for screening.
For E, we do not build molecular models for noncovalent docking (e.g.,
boronic acids). We also curated 40 patterns used by the prior version
of ZINC. SMARTS patterns are rendered using SMARTSViewer.110 (link)
interest in pan-assay interference (PAINS)58 (link) SMARTS patterns recently. We used the RDKit version53 of the Guha translation57 (link) of
the original 480 PAINS expressed in Sybyl Line Notation (SLN).58 (link) All molecules in ZINC have been annotated and
are searchable by PAINS and other SMARTS patterns. We compute a reactivity molecular property from the pattern membership
of each molecule. The reactivity categories are A) anodyne; B) clean
(PAINS-ok); C) mild (weakly reactive, typically as a nucleophile or
electrophile); D) reactive; E) unstable or irrelevant for screening.
For E, we do not build molecular models for noncovalent docking (e.g.,
boronic acids). We also curated 40 patterns used by the prior version
of ZINC. SMARTS patterns are rendered using SMARTSViewer.110 (link)
Analgesics
Biological Assay
Boronic Acids
Pain
Zinc
AmpC beta-lactamases
Boronic Acids
cDNA Library
inhibitors
Natural Products
Peptide Library
Pharmaceutical Preparations
Toxins, Biological
For boronic acid derivative experiments, mammalian peptides were dissolved in 100 mM ammonium acetate buffer and incubated for 1 h with different boronic acid-derivatized magnetic beads at room temperature. After incubation, the beads were washed with the binding buffer, and enriched glycopeptides were eluted first by incubation with a solution containing ACN:H2O:TFA (50:49:1) at 37 °C for 30 min. Then the glycopeptides were eluted two more times through incubation with 5% formic acid at 56 °C for 5 min each time. For the enrichment of glycopeptides from yeast, human cells, or mouse brain tissues using DBA, ~10 mg of peptides were used in each experiment and incubated with DBA beads in DMSO containing 0.5% TEA, and then washed five times using a buffer containing 50% DMSO and 50% 100 mM ammonium acetate (pH = 11). Glycopeptides were then eluted as described above.
For lectin enrichment, ConA and WGA-conjugated agarose beads (Vector Laboratories) were washed five times using the enrichment buffer (20 mM Tris-base, pH = 7.4, 0.15 M NaCl, 1 mM MgCl2, 1 mM CaCl2, and 1 mM MnCl2)35 (link). Peptides were dissolved in the enrichment buffer, mixed with the lectin beads, and vortexed at 37 oC for an hour. The beads were then washed again with the enrichment buffer five times before glycopeptide elution using the elution buffer (0.2 M α-methyl mannoside, 0.2 M α-methyl glucoside, 0.2 M galactose, and 0.5 M N-acetyl-d -glucosamine in PBS). The elution was performed twice with vortexing for half an hour each, and the eluents were combined.
For HILIC enrichment, SeQuant® ZIC-HILIC SPE cartridges (the Nest Group) were washed with ten column volumes of 1.0% TFA in water, followed by three washes with the loading buffer (1.0% TFA in 80% ACN, 20% H2O)38 (link)–40 (link). Peptides were loaded onto the column in the loading buffer using a slow flow rate. The column was then washed with the loading buffer three times. Glycopeptides were eluted using 1.0% TFA in water three times, and the eluents were combined.
For lectin enrichment, ConA and WGA-conjugated agarose beads (Vector Laboratories) were washed five times using the enrichment buffer (20 mM Tris-base, pH = 7.4, 0.15 M NaCl, 1 mM MgCl2, 1 mM CaCl2, and 1 mM MnCl2)35 (link). Peptides were dissolved in the enrichment buffer, mixed with the lectin beads, and vortexed at 37 oC for an hour. The beads were then washed again with the enrichment buffer five times before glycopeptide elution using the elution buffer (0.2 M α-methyl mannoside, 0.2 M α-methyl glucoside, 0.2 M galactose, and 0.5 M N-acetyl-
For HILIC enrichment, SeQuant® ZIC-HILIC SPE cartridges (the Nest Group) were washed with ten column volumes of 1.0% TFA in water, followed by three washes with the loading buffer (1.0% TFA in 80% ACN, 20% H2O)38 (link)–40 (link). Peptides were loaded onto the column in the loading buffer using a slow flow rate. The column was then washed with the loading buffer three times. Glycopeptides were eluted using 1.0% TFA in water three times, and the eluents were combined.
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ammonium acetate
Boronic Acids
Brain
Buffers
Cells
Cloning Vectors
Concanavalin A
formic acid
Galactose
Glucosamine
Glucosides
Glycopeptides
Homo sapiens
Lectin
Magnesium Chloride
Mammals
manganese chloride
methylmannoside
Mice, House
Peptides
Sepharose
Sodium Chloride
Sulfoxide, Dimethyl
Tissues
Tromethamine
Yeast, Dried
Most recents protocols related to «Boronic Acids»
Example 93
This compound was synthesized using 6-bromospiro[chromane-2,4′-piperidine]-1′-carboxamide (0.068 g, 0.21 mmol) and (1-tert-butoxycarbonylindol-3-yl)boronic acid (0.082 g, 0.31 mmol) to yield the desired compound as an off-white solid (0.076 g, 79%). Analysis: LCMS m/z=462 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 8.14 (d, J=8.3 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.76 (s, 1H), 7.45-7.36 (m, 3H), 7.35-7.28 (m, 1H), 6.91 (d, J=8.3 Hz, 1H), 5.96 (s, 2H), 3.69 (d, J=13.3 Hz, 2H), 3.20-3.08 (m, J=10.9, 10.9 Hz, 2H), 2.83 (t, J=6.7 Hz, 2H), 1.83 (t, J=6.8 Hz, 2H), 1.74-1.67 (m, 2H), 1.65 (s, 9H), 1.60-1.48 (m, 2H).
Full text: Click here
1H NMR
Boronic Acids
indole
Lincomycin
piperidine
Sulfoxide, Dimethyl
TERT protein, human
Example 92
This compound was synthesized using tert-butyl 6-bromospiro[4H-1,3-benzodioxine-2,4′-piperidine]-1′-carboxylate (0.100 g, 0.260 mmol) and (1-tert-butoxycarbonylindol-2-yl)boronic acid (0.102 g, 0.390 mmol) to yield the desired compound as an off-white foam (0.082 g, 61%). Analysis: LCMS m/z=521 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 8.11-8.04 (m, 1H), 7.59 (d, J=7.3 Hz, 1H), 7.36-7.28 (m, 1H), 7.28-7.21 (m, 2H), 7.19 (d, J=2.0 Hz, 1H), 6.93 (d, J=8.3 Hz, 1H), 6.65 (s, 1H), 4.90 (s, 2H), 3.53-3.38 (m, 4H), 1.90-1.75 (m, 4H), 1.42 (s, 9H), 1.29 (s, 9H).
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1H NMR
Boronic Acids
Lincomycin
piperidine
Sulfoxide, Dimethyl
TERT protein, human
Example 14
A mixture of tert-butyl ((3R,5S)-1-(5-(2-chloropyrimidine-4-carboxamido)-2-methylbenzo[d]thiazol-4-yl)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (Intermediate 13, 76 mg, 0.146 mmol), (2-cyano-6-methoxyphenyl)boronic acid (15.55 mg, 0.088 mmol), XPhos Pd G2 (57.6 mg, 0.073 mmol), potassium phosphate tribasic (62.2 mg, 0.293 mmol), 1,4-dioxane (1 mL), and water (0.2 mL) was purged under nitrogen and stirred at 80° C. for 2 hrs. After cooling to r.t., the reaction mixture was concentrated and TFA (1 mL) was added and the resulting mixture was stirred at r.t. for 30 minutes. The reaction mixture was then diluted with acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C26H28N7O4S (M+H)+: m/z=534.2; Found: 534.2.
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2-chloropyrimidine
acetonitrile
Boronic Acids
Carbamates
Dioxanes
Lincomycin
Nitrogen
potassium phosphate
Pyrimidines
TERT protein, human
Example 49
Synthesis of AM362-A.
To a degassed mixture of tert-butyl 5-bromoisoindoline-2-carboxylate (1 g, 3.3 mmol), 1-methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (1.12 g, 5.031 mmol) and Cs2CO3 (3.2 g, 9.9 mmol) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2 under N2 atmosphere and the mixture was heated at 95° C. overnight. The reaction mixture was diluted with DCM (25 mL) and the catalyst was removed by filtration through the celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (PE:EtOAc=80:20˜60:40) to give AM362-A (0.8 g, 76%) as a brown gum.
Compound AM362 (450 mg, 95%, a brown solid) was synthesized in a similar procedure used for AM351 from AM351-D.
Compound AM403 (250 mg, 96%, a yellow solid) was synthesized in a similar manner using the appropriately substituted boronic acid pinacol ester variant of AM362.
Full text: Click here
Anabolism
Atmosphere
Boronic Acids
Celite
Chromatography
dioxane
Esters
Filtration
pinacol
Pyrrolidines
Silica Gel
TERT protein, human
Example 31
To a solution of 4-((5-bromo-2-(4-fluorophenoxy)benzamido)methyl)benzoic acid (80 mg, 1.0 eq) and (3-cyano-5-fluorophenyl)boronic acid (59 mg, 2.0 eq) in DMF (1.2 mL) 2M Cs2CO3 (0.27 mL, 3.0 eq) and Pd(dppf)Cl2·DCM (9 mg, 0.06 eq) under nitrogen atmosphere. After stirred at 110° C. for 20 h, the mixture was filtered through celite, rinsing with ethyl acetate (20 mL). The organic phase was washed with sat. aq. sodium bicarbonate (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by flash column chromatography (Hexanes:ethyl acetate, 1:1) to obtain the acid IV-484-536 as white solid (22 mg, 25.2% yield).
1H-NMR (400 MHz, DMSO-d6): δ=12.86 (s, 1H), 8.99 (t, 1H), 8.12 (s, 1H), 8.07 (d, 2H), 8.01 (dd, 1H), 7.89 (dd, 1H), 7.84 (d, 2H), 7.39 (d, 2H), 7.27 (m, 2H), 7.16 (m, 2H), 6.99 (d, 1H), 4.54 (d, 2H).
HPLC-MS: Rt 2.23 m/z 485.1 (MH+)
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1H NMR
Acids
Atmosphere
Benzoic Acid
Bicarbonate, Sodium
Boronic Acids
brine
Celite
Chromatography
diphenyl
ethyl acetate
Hexanes
High-Performance Liquid Chromatographies
Nitrogen
Pressure
Sulfoxide, Dimethyl
Top products related to «Boronic Acids»
Sourced in United States
The XBridge C8 is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of a wide range of analytes. The column features a silica-based stationary phase with octyl (C8) functionality, providing a balance of hydrophobic and polar interactions for effective separation.
The EliteLa Chrom 70173815 is a liquid chromatography instrument manufactured by Waters Corporation. It is designed for the separation, identification, and quantification of chemical compounds in a liquid sample.
The Chrom 70173815 is a laboratory instrument designed for chromatographic separation and analysis. It is a core component of analytical workflows, enabling the separation, identification, and quantification of complex mixtures. The device performs these functions through the application of various chromatographic techniques.
Sourced in United States
Boronic acid is a class of organic compounds containing the functional group R-B(OH)2. It is a useful intermediate in organic synthesis and is commonly used in various chemical reactions and applications.
The HPLC A19/533 EliteLa Chrom 70173815 is a high-performance liquid chromatography (HPLC) system designed for laboratory use. It is equipped with a variety of features to facilitate efficient separation and analysis of complex samples.
Sourced in United States
Coumarin Boronic acid (CBA) is a chemical compound used in various laboratory applications. It is a colorless solid that is soluble in organic solvents. CBA is commonly used as a reagent for the detection and quantification of various analytes in analytical chemistry.
Sourced in United States, Italy, Japan, Germany
The Gemini C18 is a reversed-phase liquid chromatography column designed for the separation and analysis of a wide range of organic compounds. It features a fully porous silica-based stationary phase with a C18 alkyl bonded ligand. The column is capable of operating at high pressure and temperature conditions, making it suitable for a variety of analytical applications.
Sourced in Germany
Synergi C18 is a reversed-phase high-performance liquid chromatography (HPLC) column. It features a silica-based packing material with chemically bonded C18 alkyl chains, which provides effective separation of a wide range of nonpolar to moderately polar compounds.
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Taurine is a chemical compound that serves as a key component in various laboratory equipment and instruments. It is a sulfur-containing amino acid that plays a crucial role in several biological processes. Taurine is commonly used in the manufacture of specialized reagents, buffers, and solutions for scientific research and analysis.
Sourced in United States, Germany, France, United Kingdom
K2CO3 is a white, crystalline chemical compound that is commonly used in various industrial and laboratory applications. It is the potassium salt of carbonic acid and has a molecular formula of K2CO3. K2CO3 is a versatile compound with a wide range of uses, including as a pH regulator, desiccant, and in the production of certain types of glass and ceramics.
More about "Boronic Acids"
Boronic acids, also known as organoboron compounds, are a versatile class of compounds containing the functional group -B(OH)2.
These chemical entities have gained significant attention in the realms of organic synthesis, medicinal chemistry, materials science, and biochemistry.
One of the key applications of boronic acids is their use in Suzuki cross-coupling reactions, a widely employed method in organic synthesis.
Additionally, boronic acids exhibit unique properties, such as the ability to form cyclic esters with diols and to interact with various nucleophiles, making them valuable tools for researchers.
Boronic acid-based compounds have found applications in diverse areas, including the development of pharmaceutical agents, sensors, and materials.
For instance, Coumarin Boronic Acid (CBA) is a boronic acid derivative that has been investigated for its potential use in fluorescent probes and bioimaging applications.
When working with boronic acids, researchers can utilize advanced platforms like PubCompare.ai, which leverages artificial intelligence to identify the most reproducible and accurate protocols from published literature, preprints, and patents.
This can help optimize workflows and enhance research efficiency.
Furthermore, related terms and techniques, such as HPLC (High-Performance Liquid Chromatography), C8 and C18 stationary phases (e.g., XBridge C8, Gemini C18, Synergi C18), and chemical additives (e.g., Taurine, K2CO3), can be employed in the analysis and purification of boronic acid-containing compounds.
By exploring the versatility and applications of boronic acids, researchers can unlock new possibilities in their respective fields, advancing our understanding and utilization of these remarkable chemical entities.
These chemical entities have gained significant attention in the realms of organic synthesis, medicinal chemistry, materials science, and biochemistry.
One of the key applications of boronic acids is their use in Suzuki cross-coupling reactions, a widely employed method in organic synthesis.
Additionally, boronic acids exhibit unique properties, such as the ability to form cyclic esters with diols and to interact with various nucleophiles, making them valuable tools for researchers.
Boronic acid-based compounds have found applications in diverse areas, including the development of pharmaceutical agents, sensors, and materials.
For instance, Coumarin Boronic Acid (CBA) is a boronic acid derivative that has been investigated for its potential use in fluorescent probes and bioimaging applications.
When working with boronic acids, researchers can utilize advanced platforms like PubCompare.ai, which leverages artificial intelligence to identify the most reproducible and accurate protocols from published literature, preprints, and patents.
This can help optimize workflows and enhance research efficiency.
Furthermore, related terms and techniques, such as HPLC (High-Performance Liquid Chromatography), C8 and C18 stationary phases (e.g., XBridge C8, Gemini C18, Synergi C18), and chemical additives (e.g., Taurine, K2CO3), can be employed in the analysis and purification of boronic acid-containing compounds.
By exploring the versatility and applications of boronic acids, researchers can unlock new possibilities in their respective fields, advancing our understanding and utilization of these remarkable chemical entities.