All metabolite reference standards underwent a two-step derivatization procedure. Therefore 1 mg of each standard was dissolved in a solution of 1 ml methanol:water:isopropanol (2.5:1:1 v/v). Then 10 μl of each standard solution were taken out and evaporated to dryness. First, methoximation was performed to inhibit the ring formation of reducing sugars, protecting also all other aldehydes and ketones. A solution of 40 mg/ml O-methylhydroxylamine hydrochloride, (CAS: [593-56-6]; Formula CH5NO.HCl; Sigma-Aldrich No. 226904 (98%)) in pyridine (99.99%) was prepared. The dried standards and 10 μl of the O-methylhydroxylamine reagent solution were mixed for 30 s in a vortex mixer and subsequently shaken for 90 minutes at 30°C. Afterwards, 90μl of N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) with 1% trimethylchlorosilane (TMCS) (1 ml bottles, Pierce, Rockford IL) was added and shaken at 37°C for 30 min for trimethylsilylation of acidic protons to increase volatility of metabolites. A mixture of internal retention index (RI) markers was prepared using fatty acid methyl esters (FAME markers) of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28 and C30 linear chain length, dissolved in chloroform at a concentration of 0.8 mg/ml (C8-C16) and 0.4 mg/ml (C18-C30). 2 μl of this RI mixture were added to the reagent solutions, transferred to 2 mL glass crimp amber autosampler vials. Data acquisition parameters are given in table 1 . Subsequent to data processing using the instrument manufacturer’s software programs, spectra and retention indices were manually curated into the new Leco FiehnLib (359-008-100) or automatically transferred by Agilent to the new Agilent FiehnLib (G1676AA).
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Esters
Esters
Esters are a diverse class of organic compounds formed by the reaction of an alcohol and an acid, resulting in the characteristic ester linkage.
They play a vital role in various fields, including chemistry, biology, and industry, with applications ranging from solvents and fragrances to plasticizers and pharmaceuticals.
Explore the nuanced world of esters with PubCompare.ai's cutting-edge platform, which seamlessly integrates intelligent protocol comparisons and cutting-edge research tools to enhance reproducibility and optimize your experiments.
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They play a vital role in various fields, including chemistry, biology, and industry, with applications ranging from solvents and fragrances to plasticizers and pharmaceuticals.
Explore the nuanced world of esters with PubCompare.ai's cutting-edge platform, which seamlessly integrates intelligent protocol comparisons and cutting-edge research tools to enhance reproducibility and optimize your experiments.
Experince the future of protocol discovery today.
Most cited protocols related to «Esters»
Acids
Aldehydes
Amber
Cardiac Arrest
Chloroform
Esters
Fatty Acids
Isopropyl Alcohol
Ketones
Methanol
methoxyamine
Protons
pyridine
Retention (Psychology)
Sugars
trimethylchlorosilane
Volatility
Alkenes
Conferences
Esters
Glycerin
Head
Lipids
Acetylcysteine
Adult
Anabolism
Animals
Antioxidants
Brain
Cells
Diet, Formula
Esters
Gastrin-Secreting Cells
Glutathione
HEPES
Lipid Peroxidation
Muscle Rigidity
Neurons
Oxidative Damage
Oxidative Stress
Permeability
Protoplasm
Pyramidal Cells
Reduced Glutathione
Susceptibility, Disease
Tissue, Membrane
Tissues
Cells
Esters
Gene Expression
Gene Library
Genes
Retina
Single-Cell Analysis
Trees
Bath
Brain
carboxy-seminaphthorhodaminefluoride
Cells
Cloning Vectors
Codon
Cortex, Cerebral
Esters
Formaldehyde
Genes
Lentivirus
Light
Mammals
Microelectrodes
Microscopy, Confocal
Mus
Mutagenesis
Nervousness
Neurons
Operative Surgical Procedures
Perfusion
Plasmids
Transfection
Trypan Blue
Virus
Virus Diseases
Most recents protocols related to «Esters»
Example 21
Complex Em9-i:
A solution of 0.17 g of complex Em9-s in 2000 ml acetonitril are irradiated at 15° C. for 9.5 h with a blacklight-blue-lamp (Osram, L18W/73, λmax=370-380 nm). The solvent is removed in vacuo. The residue is purified by chromatography (cyclohexane/acetic ester). 0.055 g of Em9-i (32%, contaminated with traces of a further complex) are obtained as well as 0.075 g of reisolated Em9-s (44%) are reisolated.
1H-NMR [CD2Cl2, 400 MHz, sample comprises traces of a further complex observable for example at 0.77 (m), 0.83 (d), 1.04 (d), 1.21 (m), 1.92 (sept), 2.34 (sept), 7.20-7.23 (m), 7.31-7.34 (m)]:
δ=0.65 (d, 3H), 0.77 (d, 3H), 0.85 (d, 3H), 0.97 (d, 3H), 0.98 (d, 3H), 1.02 (d, 3H), 1.13 (d, 6H), 1.82 (sept, 1H), 2.33 (sept, 1H), 2.54 (sept, 1H), 2.67 (sept, 1H), 3.04 (s, 3H), 6.09 (dd, 2H), 6.37 (td, 1H), 6.40-6.44 (m, 3H), 6.50 (m, 1H), 6.59 (d, 1H), 6.61 (td, 1H), 6.68 (d, 1H), 6.70 (d, 1H), 6.72 (d, 1H), 6.86 (d, 1H), 6.96 (br.s, 1H), 7.14 (me, 2H), 7.20-7.23 (m, 1H), 7.23-7.31 (m, 3H), 7.44-7.50 (m, 3H).
MS (Maldi):
m/e=979 (M+H)+
photoluminescence (in film, 2% in PMMA):
λmax=457, 485 nm, CIE: (0.17; 0.26)
The photoluminescence quantum efficiency of the isomer Em9-i has the 1.14-fold value of the quantum efficiency of the isomer Em9-s.
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1H NMR
carbene
Chromatography
Cyclohexane
Esters
Isomerism
NADH Dehydrogenase Complex 1
Polymethyl Methacrylate
Solvents
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Suby's G solution
Example 14
Cephem Conjugates
Cephem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [15690-38-7] is converted to a hydroxymethyl intermediate containing a side chain and protecting ester of choice as described in the literature (WO 96/04247). A cannabinoid (CBD) is converted to the O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). The hydroxymethyl and O-chloromethyl intermediates are reacted under previously reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to generate the acetal link. Removal of the diphenylmethyl ester protecting group gives the product.
Carbacephem Conjugates
Carbacephem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [177472-75-2] is converted to a hydroxymethyl intermediate containing a side chain and protecting ester of choice as described in the literature (WO 96/04247). A cannabinoid (CBD) is converted to the O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). The hydroxymethyl and O-chloromethyl intermediates are reacted under previously reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to generate the acetal link. Removal of the diphenylmethyl ester protecting group gives the product.
Penem Conjugates
Penem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. A cannabinoid (CBD) is converted to its O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). This intermediate is reacted with a hydroxymethyl penem [88585-78-8] under reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to form the acetal link. Removal of the silyl ether and allyl ester protecting groups under standard conditions gives the product.
Carbapenem Conjugates
Carbapenem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. A cannabinoid (CBD) is converted to its O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). This intermediate is reacted with a hydroxymethyl carbapenem [118990-99-1] under reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to form the acetal link. Removal of the allyl protecting groups under standard conditions gives the product.
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Acetals
Cannabinoids
carbacephems
Carbapenems
Esters
Ethers
Monobactams
Penem
Example 1
<Step (A): Synthesis of porous particle having glycidyl group>
27.8 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 11.3 g of glycerin-1,3-dimethacrylate (trade name: NK Ester 701, SHIN-NAKAMURA CHEMICAL Co., Ltd.), and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were dissolved in 58.7 g of diethyl succinate as a diluent, and nitrogen gas was bubbled for 30 minutes to provide an oil phase.
Next, separately from the oil phase, 10.0 g of PVA-224 (manufactured by Kuraray Co., Ltd., polyvinyl alcohol having a degree of saponification of 87.0% to 89.0%) as a dispersion stabilizer and 10.0 g of sodium chloride as a salting-out agent were dissolved in 480 g of ion exchanged water to provide an aqueous phase.
The aqueous phase and the oil phase were placed in a separable flask and dispersed at a rotation speed of 430 rpm for 20 minutes using a stirring rod equipped with a half-moon stirring blade, then the inside of the reactor was purged with nitrogen, and the reaction was carried out at 60° C. for 16 hours.
After that, the resulting polymer was transferred onto a glass filter and thoroughly washed with hot water at about 50 to 80° C., denatured alcohol, and water in the order presented to obtain 100.4 g of a porous particle (carrier al).
The amount of glycidyl methacrylate used was 79.8 mol % based on the total amount of the monomers, and the amount of glycerin-1,3-dimethacrylate used was 20.2 mol % based on the total amount of the monomers.
<Step (B): Introduction reaction of alkylene group>
98 g of the carrier α1 was weighed onto a glass filter and thoroughly cleaned with diethylene glycol dimethyl ether. After cleaning, the carrier α1 was placed in a 1 L separable flask, 150 g of diethylene glycol dimethyl ether and 150 g (920 mol % based on glycidyl methacrylate) of 1,4-butanediol were placed in the separable flask, and stirring and dispersion were carried out.
After that, 1.5 ml of a boron trifluoride diethyl ether complex was added, the temperature was raised to 80° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 4 hours.
The mixture was cooled, then the porous particle (carrier β1) bonded to a diol compound including an alkylene group in the structure thereof was collected by filtration and then washed with 1 L of ion exchanged water to obtain 152 g of a carrier β1.
The progress of the reaction was confirmed by the following procedure.
A part of the dry porous particle into which an alkylene group had been introduced was mixed with potassium bromide, and the resulting mixture was pelletized by applying a pressure and then measured using FT-IR (trade name: Nicolet (registered trademark) iS10, manufactured by Thermo Fisher Scientific Inc.) to check the height of an absorbance peak at 908 cm−1 due to the glycidyl group in the infrared absorption spectrum.
As a result, no absorbance peak at 908 cm−1 was observed by FT-IR.
<Step (C): Introduction Reaction of Glycidyl Group>
150 g of the carrier β1 was weighed onto a glass filter and thoroughly cleaned with dimethylsulfoxide.
After cleaning, the carrier β1 was placed in a separable flask, 262.5 g of dimethyl sulfoxide and 150 g of epichlorohydrin were added, the resulting mixture was stirred at room temperature, 37.5 ml of a 30% sodium hydroxide aqueous solution (manufactured by KANTO CHEMICAL CO., INC.) was further added, and the resulting mixture was heated to 30° C. and stirred for 6 hours.
After completion of the reaction, the obtained product was transferred onto a glass filter and thoroughly washed with water, acetone, and water in the order presented to obtain 172 g of a porous particle into which a glycidyl group had been introduced (carrier γ1).
The introduction density of the glycidyl group in the obtained carrier γ1 was measured by the following procedure.
5.0 g of the carrier γ1 was sampled, and the dry mass thereof was measured and as a result, found to be 1.47 g. Next, the same amount of the carrier γ1 was weighed into a separable flask and dispersed in 40 g of water, 16 mL of diethylamine was added while stirring at room temperature, and the resulting mixture was heated to 50° C. and stirred for 4 hours. After completion of the reaction, the reaction product was transferred onto a glass filter and thoroughly washed with water to obtain a porous particle A into which diethylamine had been introduced.
The obtained porous particle A was transferred into a beaker and dispersed in 150 mL of a 0.5 mol/L potassium chloride aqueous solution, and titration was carried out using 0.1 mol/L hydrochloric acid with the point at which the pH reached 4.0 as the neutralization point.
From this, the amount of diethylamine introduced into the porous particle A into which diethylamine had been introduced was calculated, and the density of the glycidyl group of the carrier γ1 was calculated from the following expression.
As a result, the density of the glycidyl group was 880 μmol/g.
Density(μmol/g) of glycidyl group={0.1×volume(μL) of hydrochloric acid at neutralization point/dry mass(g) of porous particle into which glycidyl group has been introduced}<Step (D): Introduction Reaction of Polyol>
150 g of the carrier γ1, 600 mL of water, and 1000 g (13000 mol % based on glycidyl group) of D-sorbitol (log P=−2.20, manufactured by KANTO CHEMICAL CO., INC.) were placed in a 3 L separable flask and stirred to form a dispersion.
After that, 10 g of potassium hydroxide was added, the temperature was raised to 60° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 15 hours.
The mixture was cooled, and then the reaction product was collected by filtration and washed thoroughly with water to obtain 152 g of a porous particle into which polyol had been introduced (carrier 61).
The obtained carrier 61 was classified into 16 to 37 μm using a sieve to obtain 140.5 g of a packing material 1.
<Evaluation of Alkali Resistance>
The alkali resistance was evaluated by calculating the amount of a carboxy group produced by hydrolysis of sodium hydroxide according to the following procedure.
First, 4 g of the packing material was dispersed in 150 mL of a 0.5 mol/L potassium chloride aqueous solution, and titration was carried out using 0.1 mol/L sodium hydroxide aqueous solution with the point at which the pH reached 7.0 as the neutralization point. From this, the amount of a carboxy group before hydrolysis included in the packing material was calculated from the following expression.
Amount(μmol/mL) of carboxy group=0.1×volume(μL) of sodium hydroxide aqueous solution at the time of neutralization/apparent volume (mL) of packing material
Here, the apparent volume of the packing material is the volume of the packing material phase measured after preparing a slurry liquid by dispersing 4 g of the packing material in water, transferring the slurry liquid to a graduated cylinder, and then allowing the same to stand for a sufficient time.
Subsequently, 4 g of the packing material was weighed into a separable flask, 20 mL of a 5 mol/L sodium hydroxide aqueous solution was added, and the resulting mixture was treated at 50° C. for 20 hours while stirring at 200 rpm. The mixture was cooled, then the packing material was collected by filtration, then washed with a 0.1 mol/L HCl aqueous solution and water in the order presented, and the amount of a carboxy group contained in the obtained packing material was calculated by the same method as above. From the difference between the amount of a carboxy group before and that after the reaction with the 5 mol/L sodium hydroxide aqueous solution, the amount of a carboxy group produced by the reaction with the 5 mol/L sodium hydroxide aqueous solution was calculated. As a result, the amount of a carboxy group produced was 21 μmol/mL.
If the amount of a carboxy group produced is 40 μmol/mL or less, the alkali resistance is considered to be high.
<Evaluation of Non-Specific Adsorption>
The obtained packing material was packed into a stainless steel column (manufactured by Sugiyama Shoji Co., Ltd.) having an inner diameter of 8 mm and a length of 300 mm by a balanced slurry method. Using the obtained column, a non-specific adsorption test was carried out by the method shown below.
The column packed with the packing material was connected to a Shimadzu Corporation HPLC system (liquid feed pump (trade name: LC-10AT, manufactured by Shimadzu Corporation), autosampler (trade name: SIL-10AF, manufactured by Shimadzu Corporation), and photodiode array detector (trade name: SPD-M10A, manufactured by Shimadzu Corporation)), and a 50 mmol/L sodium phosphate buffer aqueous solution as a mobile phase was passed at a flow rate of 0.6 mL/min.
Using the same sodium phosphate aqueous solution as the mobile phase as a solvent, their respective sample solutions of 0.7 mg/mL thyroglobulin (Mw of 6.7×105), 0.6 mg/mL γ-globulin (Mw of 1.6×105), 0.96 mg/mL BSA (Mw of 6.65×104), 0.7 mg/mL ribonuclease (Mw of 1.3×104), 0.4 mg/mL aprotinin (Mw of 6.5×103), and 0.02 mg/mL uridine (Mw of 244) (all manufactured by Merck Sigma-Aldrich) are prepared, and 10 μL of each is injected from the autosampler.
The elution time of each observed using the photodiode array detector at a wavelength of 280 nm was compared to confirm that there was no contradiction between the order of elution volume and the order of molecular weight size.
As a result, the elution volumes of the samples from the column packed with the packing material 1 were 8.713 mL, 9.691 mL, 9.743 mL, 10.396 mL, 11.053 mL, and 11.645 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced. When there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof, there was no non-specific adsorption, which is indicated as 0 in Table 1, and when there was a contradiction therebetween, non-specific adsorption was induced, which is thus indicated as X.
The porous particle (carrier al) obtained in the same manner as in Example 1 was subjected to the step D of Example 1.
<Step (D): Introduction Reaction of Polyol>
98 g of carrier al, 600 mL of water, and 1000 g (3050 mol % based on glycidyl group) of D-sorbitol (manufactured by KANTO CHEMICAL CO., INC.) were placed in a 3 L separable flask and stirred to form a dispersion.
After that, 10 g of potassium hydroxide was added, the temperature was raised to 60° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 15 hours.
The mixture was cooled, and then the reaction product was collected by filtration and washed thoroughly with water to obtain 130 g of a porous particle into which a polyol had been introduced (carrier δ7).
The carrier δ7 was classified into 16 to 37 μm using a sieve to obtain 115 g of a packing material 7.
The alkali resistance of the obtained packing material 7 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced in the packing material 7 was 120.3 μmol/mL, resulting in poor alkali resistance.
Further, the non-specific adsorption of the obtained packing material 7 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.606 mL, 9.769 mL, 9.9567 mL, 10.703 mL, 11.470 mL, and 12.112 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
Example 2
A porous particle (carrier al) was obtained in the same manner as in Example 1, and then a packing material 2 was obtained as follows.
98 g of the carrier α1 was weighed onto a glass filter and thoroughly cleaned with diethylene glycol dimethyl ether.
After cleaning, the porous particle was placed in a 1 L separable flask, 150 g of diethylene glycol dimethyl ether and 150 g (580 mol % based on the glycidyl group) of 1,4-cyclohexanedimethanol were placed in the separable flask, and stirring and dispersion were carried out.
After that, 1.5 ml of a boron trifluoride diethyl ether complex was added, the temperature was raised to 80° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 4 hours.
The mixture was cooled, then the resulting porous particle (carrier $2) bonded to a diol compound including an alkylene group in the structure thereof was collected by filtration and then washed with 1 L of ion exchanged water to obtain 165 g of a carrier 32.
The progress of the reaction was confirmed by the following procedure.
A part of the dry porous particle into which an alkylene group had been introduced was mixed with potassium bromide, and the resulting mixture was pelletized by applying a pressure and then measured using FT-IR (trade name: Nicolet (registered trademark) iS10, manufactured by Thermo Fisher Scientific Inc.) to check the height of a absorbance peak at 908 cm−1 due to the glycidyl group in the infrared absorption spectrum.
As a result, no absorbance peak at 908 cm−1 was observed by FT-IR.
<Step (C): Introduction Reaction of Glycidyl Group>
150 g of the carrier $2 was weighed onto a glass filter and thoroughly cleaned with dimethylsulfoxide. After cleaning, the carrier $2 was placed in a separable flask, 262.5 g of dimethyl sulfoxide and 150 g of epichlorohydrin were added, the resulting mixture was stirred at room temperature, 37.5 ml of a 30% sodium hydroxide aqueous solution (manufactured by KANTO CHEMICAL CO., INC.) was further added, and the resulting mixture was heated to 30° C. and stirred for 6 hours. After completion of the reaction, the porous particle was transferred onto a glass filter and thoroughly washed with water, acetone, and water in the order presented to obtain 180 g of a porous particle into which a glycidyl group had been introduced (carrier γ2).
The introduction density of the glycidyl group in the obtained carrier γ2 was measured in the same manner as in Example 1. As a result, the density of the glycidyl group was 900 μmol/g.
<Step (D): Introduction Reaction of Polyol>
150 g of the carrier γ2 was weighed onto a glass filter and thoroughly cleaned with diethylene glycol dimethyl ether. After cleaning, the carrier γ2 was placed in a 1 L separable flask, 150 g of diethylene glycol dimethyl ether and 150 g (5760 mol % based on the glycidyl group) of ethylene glycol (log P=−1.36) were placed in the separable flask, and stirring and dispersion were carried out. After that, 1.5 mL of a boron trifluoride diethyl ether complex was added, the temperature was raised to 80° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 4 hours. The mixture was cooled, and then the reaction product was collected by filtration and washed thoroughly with water to obtain 152 g of a polyol-introduced porous particle (carrier δ2). The carrier δ2 was classified into 16 to 37 μm using a sieve to obtain 140.5 g of a packing material 2.
The alkali resistance of the obtained packing material 2 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced was 15.2 μmol/mL, and it was confirmed that the packing material 2 had excellent alkali resistance.
Further, the non-specific adsorption of the obtained packing material 2 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.814 mL, 9.635 mL, 9.778 mL, 10.37 mL, 10.898 mL, and 12.347 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
A packing material 8 was obtained in the same manner as in Example 1 except that 150 g of ethylene glycol was used instead of 1,4-butanediol as an alkylene group-introducing agent.
The alkali resistance of the obtained packing material 8 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced in the packing material 8 was 108.4 μmol/mL, resulting in poor alkali resistance.
Further, the non-specific adsorption of the obtained packing material 8 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 9.708 mL, 9.8946 mL, 10.6452 mL, 11.5374 mL, and 12.1656 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
Example 3
A carrier γ2 was obtained in the same manner as in Example 2.
150 g of the obtained carrier γ2 was weighed onto a glass filter and thoroughly cleaned with diethylene glycol dimethyl ether.
After cleaning, the porous particle was placed in a 1 L separable flask, 150 g of diethylene glycol dimethyl ether and 150 g of polyethylene glycol #200 (manufactured by KANTO CHEMICAL CO., INC., average molecular weight of 190 to 210, log P is unclear, but the close compound tetraethylene glycol (Mw of 194) has a log P of −2.02) (1790 mol % based on glycidyl group) were placed in the separable flask, and stirring and dispersion were carried out.
After that, 1.5 mL of a boron trifluoride diethyl ether complex was added, the temperature was raised to 80° C. while stirring at 200 rpm, and the resulting mixture was subjected to the reaction for 4 hours.
The mixture was cooled, and then the reaction product was collected by filtration and washed thoroughly with water to obtain 152 g of a porous particle into which a polyol had been introduced (carrier 63).
The carrier δ3 was classified into 16 to 37 μm using a sieve to obtain 140.5 g of a packing material 3.
The alkali resistance of the obtained packing material 3 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced was 16.1 μmol/mL, and it was confirmed that the packing material 3 had excellent alkali resistance.
Further, the non-specific adsorption of the obtained packing material 3 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.517 mL, 9.241 mL, 9.47 mL, 10.034 mL, 10.484 mL, and 11.927 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
A packing material 9 was obtained in the same manner as in Example 2 except that no glycidyl group was introduced and no polyol was introduced. That is, the carrier $2 obtained in the step (B) of Example 2 was used as the packing material 9.
The non-specific adsorption of the obtained packing material 9 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.590 mL, 10.316 mL, 9.603 mL, 10.484 mL, 13.863 mL, and 12.861 mL, and it was confirmed that there was a contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that non-specific adsorption was induced. Because of this, the alkali resistance was not evaluated.
Example 4
A packing material 4 was obtained in the same manner as in Example 3 except that 33.2 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 5.9 g of glycerin-1,3-dimethacrylate (trade name: NK Ester 701, SHIN-NAKAMURA CHEMICAL Co., Ltd.), 58.7 g of diethyl succinate, and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were used to provide an oil phase. The amount of glycidyl methacrylate used was 90.0 mol % based on the total amount of the monomers, and the amount of glycerin-1,3-dimethacrylate used was 10.0 mol % based on the total amount of the monomers.
The alkali resistance of the obtained packing material 4 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced was 11.5 μmol/mL, and it was confirmed that the packing material 4 had excellent alkali resistance.
Further, the non-specific adsorption of the obtained packing material 4 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 7.52 mL, 8.214 mL, 8.451 mL, 9.062 mL, 9.511 mL, and 11.915 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
A packing material 10 was obtained in the same manner as in Example 1 except that 150 g (480 mol % based on glycidyl methacrylate) of 1,10-decanediol was used instead of 1,4-butanediol as an alkylene group-introducing agent.
The non-specific adsorption of the obtained packing material 10 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 9.991 mL, 10.15 mL, 10.063 mL, 10.691 mL, 12.172 mL, and 11.531 mL, and it was confirmed that there was a contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that non-specific adsorption was induced. Because of this, the alkali resistance was not evaluated.
Example 5
A packing material 5 was obtained in the same manner as in Example 3 except that 21.5 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 17.6 g of glycerin-1,3-dimethacrylate (trade name: NK Ester 701, SHIN-NAKAMURA CHEMICAL Co., Ltd.), 58.7 g of diethyl succinate, and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were used to provide an oil phase.
The amount of glycidyl methacrylate used was 66.2 mol % based on the total amount of the monomers, and the amount of glycerin-1,3-dimethacrylate used was 33.8 mol % based on the total amount of the monomers.
The alkali resistance of the obtained packing material 5 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced was 18.3 μmol/mL, and it was confirmed that the packing material 5 had excellent alkali resistance.
Further, the non-specific adsorption of the obtained packing material 5 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.692 mL, 9.434 mL, 9.625 mL, 10.236 mL, 10.759 mL, and 12.457 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
A packing material 11 was obtained in the same manner as in Example 3 except that 13.7 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 25.4 g of glycerin-1,3-dimethacrylate (trade name: NK Ester 701, SHIN-NAKAMURA CHEMICAL Co., Ltd.), 58.7 g of diethyl succinate, and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were used to provide an oil phase. The amount of glycidyl methacrylate used was 46.4 mol % based on the total amount of the monomers, and the amount of glycerin-1,3-dimethacrylate used was 53.6 mol % based on the total amount of the monomers.
The non-specific adsorption of the obtained packing material 11 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 8.872 mL, 10.131 mL, 9.82 mL, 10.422 mL, 12.782 mL, and 12.553 mL, and it was confirmed that there was a contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that non-specific adsorption was induced. Because of this, the alkali resistance was not evaluated.
It was confirmed that the exclusion limit molecular weights of the packing materials obtained in Examples 1 to 6 and Comparative Examples 1 to 5 were all 1,000,000 or more.
Example 6
A packing material 6 was obtained in the same manner as in Example 3 except that 33.2 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 5.9 g of ethylene glycol dimethacrylate (trade name: NK Ester 1G, SHIN-NAKAMURA CHEMICAL Co., Ltd.), 29.3 g of butyl acetate, 29.3 g of chlorobenzene, and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were used to provide an oil phase. The amount of glycidyl methacrylate used was 88.7 mol % based on the total amount of the monomers, and the amount of ethylene glycol dimethacrylate used was 11.3 mol % based on the total amount of the monomers.
The alkali resistance of the obtained packing material 6 was evaluated in the same manner as in Example 1. As a result, the amount of a carboxy group produced was 12.5 μmol/mL, and it was confirmed that the packing material 6 had excellent alkali resistance.
Further, the non-specific adsorption of the obtained packing material 6 was evaluated in the same manner as in Example 1. As a result, the elution volumes of the samples were 9.613 mL, 10.427 mL, 10.444 mL, 11.066 mL, 11.582 mL, and 12.575 mL, and it was confirmed that there was no contradiction between the order of the molecular weights of the samples and the order of the elution volumes thereof and that no non-specific adsorption was induced.
A packing material 12 was obtained in the same manner as in Example 3 except that 37.1 g of glycidyl methacrylate (trade name: Blemmer G (registered trademark) manufactured by NOF Corporation), 2.0 g of glycerin-1,3-dimethacrylate (trade name: NK Ester 701, SHIN-NAKAMURA CHEMICAL Co., Ltd.), 58.7 g of diethyl succinate, and 1.9 g of 2,2′-azobis(2,4-dimethylvaleronitrile) were used to provide an oil phase. The amount of glycidyl methacrylate used was 96.7 mol % based on the total amount of the monomers, and the amount of glycerin-1,3-dimethacrylate used was 3.3 mol % based on the total amount of the monomers.
Packing into a stainless steel column using the obtained packing material 12 was attempted. However, the back pressure was high, making liquid feeding difficult, and this made it impossible to carry out the packing. Because of this, neither of the evaluations was able to be carried out.
Results of the above Examples and Comparative Examples are shown in Table 1.
From the above results, by adopting the configuration of the present invention, a packing material having suppressed non-specific adsorption and high alkali resistance can be obtained.
When no hydrophobic portion is provided or when the alkylene chain is short, the alkali resistance is low as shown in Comparative Examples 1 and 2. In addition, it was found that when the alkylene chain is too long or when no hydrophilic portion is provided, the hydrophobicity is strong, and non-specific adsorption is induced as shown in Comparative Examples 3 and 4. In addition, in Comparative Example 5 having many repeating units derived from a polyfunctional monomer, it was found that non-specific adsorption was induced, and in Comparative Example 6 having fewer repeating units derived from a polyfunctional monomer, it was found that the back pressure applied to the apparatus was high, making column packing difficult.
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A 300
Acetone
Adsorption
Alkalies
Anabolism
Aprotinin
boron trifluoride
Buffers
butyl acetate
butylene
Butylene Glycols
chlorobenzene
COMP protocol
Cyclohexane
cyclohexanedimethanol
diethylamine
diethyl succinate
diglyme
Epichlorohydrin
Esters
Ethanol
ethylene dimethacrylate
Ethylenes
Ethyl Ether
Filtration
G 130
gamma-Globulin
Gel Chromatography
Glycerin
glycidyl methacrylate
Glycol, Ethylene
High-Performance Liquid Chromatographies
Hydrochloric acid
Hydrolysis
Nitrogen
Polyethylene Glycols
Polymers
polyol
Polyvinyl Alcohol
potassium bromide
Potassium Chloride
potassium hydroxide
Pressure
Ribonucleases
Sodium Hydroxide
sodium phosphate
Solvents
Sorbitol
Stainless Steel
Sulfoxide, Dimethyl
tetraethylene glycol
Thyroglobulin
Titrimetry
Uridine
Example 125
Methyl 4-((5-(benzyloxy)-2-methoxyphenyl)(ethyl)amino)butanoate (184). 5-(Benzyloxy)-N-ethyl-2-methoxyaniline (146) (0.681 g, 2.65 mmol), DIEA (0.92 mL, 5.3 mmol), and methyl 4-iodobutyrate (0.72 mL, 5.3 mmol) in DMF (5 mL) were stirred at 70° C. for 5 days. The reaction mixture was cooled to rt, diluted with EtOAc (60 mL), washed with water (4×50 mL), brine (75 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 184 (0.72 g, 76%) as a dark amber oil.
Methyl 4-(ethyl(5-hydroxy-2-methoxyphenyl)amino)butanoate (186). Ester 184 (0.72 g, 2.0 mmol) was stirred under reflux with 6 mL of water and 6 mL of conc HCl for 1.5 hrs and then evaporated to dryness to give acid 185 as a brown gum. The crude acid was dissolved in 50 mL of methanol containing 1 drop (cat.) of methanesulfonic acid ant the solution was kept for 2 hrs at rt. After that the mixture was concentrated in vacuum and the residue was mixed with 20 mL of saturated NaHCO3. The product was extracted with EtOAc (3×40 mL). The extract was washed with brine (40 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 186 (0.444 g, 83%) as a brown oil.
N-(6-(dimethylamino)-9-(4-(ethyl(4-methoxy-4-oxobutyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (187). To a stirred suspension of tetramethylrhodamine ketone 101 (0.234 g, 0.830 mmol) in 10 mL of dry chloroform was added oxalyl chloride (72 μL, 0.82 mmol) upon cooling to 0-5° C. The resulting red solution was stirred for 0.5 h at 5° C., and the solution of compound 186 (0.222 g, 0.831 mmol) in dry chloroform (5 mL) was introduced. The reaction was allowed to heat to rt, stirred for 72 h, diluted with CHCl3 (100 mL and washed with sat. NaHCO3 solution (2×30 mL) The organic layer was extracted with 5% HCl (3×25 mL). The combined acid extract was washed with CHCl3 (2×15 mL; discarded), saturated with sodium acetate and extracted with CHCl3 (5×30 mL). The extract was washed with brine (50 mL), dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with CHCl3/MeOH/AcOH/H2O (100:20:5:1)), eluant: CHCl3/MeOH/AcOH/H2O (100:20:5:1) to give the product 187 (0.138 g, 29%) as a purple solid.
4-((4-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-hydroxy-2-methoxyphenyl)(ethyl)amino)butanoate (188). Methyl ester 187 (0.136 g, 0.240 mmol) was dissolved in 5 mL of 1M KOH (5 mmol). The reaction mixture was kept at rt for 1.5 hrs and the acetic acid (1 mL) was added. The mixture was extracted with CHCl3 (4×30 mL), and combined extract was washed with brine (20 mL), filtered through the paper filter and. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with MeCN/H2O (4:1)), eluant: MeCN/H2O/AcOH/(4:1:1) to give the product 188 (0.069 g, 98%) as a purple solid.
N-(6-(dimethylamino)-9-(4-((4-(2,5-dioxopyrrolidin-1-yloxy)-4-oxobutyl)(ethyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (189). To a solution of the acid 188 (69 mg, 0.12 mmol) in DMF (2 mL) and DIEA (58 μL, 0.33 mmol) was added N-hydroxysuccinimide trifluoroacetate (70 mg, 0.33 mmol). The reaction mixture was stirred for 30 min, diluted with chloroform (100 mL) and washed with water (5×50 mL), brine (50 mL), filtered through paper and concentrated in vacuum. The crude product was purified by precipitation from CHCl3 solution (5 mL) with ether (20 mL) to give compound 189 (55 mg, 67%) as a purple powder.
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Acetic Acid
Acids
Amber
Anabolism
Bicarbonate, Sodium
brine
Chlorides
Chloroform
Chromatography
Esters
Ethyl Ether
Hydroxyl Radical
Ketones
methanesulfonic acid
Methanol
N,N-diisopropylethylamine
N-hydroxysuccinimide
oxalyl chloride
Powder
Silica Gel
Sodium Acetate
tetramethylrhodamine
Trifluoroacetate
Vacuum
Example 37
To improve inhibition potency relative to FAAH, various portions of the t-TUCB molecule were modified to identify potential FAAH pharmacophores. The 4-trifluoromethoxy group on t-TUCB was modified to the unsubstituted ring (A-3), 4-fluorophenyl (A-2) or 4-chlorophenyl (A-26). Potency on both sEH and FAAH increased as the size and hydrophobicity of the para position substituent increased, with 4-trifluoromethoxy being the most potent on both enzymes. Substituting the aromatic ring for a cyclohexane (A-3) or adamantane (A-4) resulted in a complete loss in activity against FAAH. Results are summarized in Table 1 below.
Next, the center portion of the molecule was modified to further investigate the specificity of t-TUCB on FAAH. Switching the cyclohexane linker to a cis conformation (A-5) resulted in a 20-fold loss of potency while removing the ring and replacing it with a butane chain (A-6) resulted in a completely inactive compound. While this suggests the compound must fit a relatively specific conformation in the active site to be active, we found the aromatic linker had essentially the same potency on FAAH (A-7). Although many potent urea-based FAAH inhibitors have a piperidine as the carbamoylating nitrogen, the modification to piperidine here reduced potency 13-fold. Results are summarized in Table 2 below.
Since none of the modifications at this point improved potency towards FAAH, we focused on the benzoic acid portion of the molecule as shown in Table 3. To determine the importance of the terminal acid, the corresponding aldehyde (A-20) and alcohol (A-24) in addition to the amide (A-19) and nitrile (A-11) were tested. While the amide had slightly improved potency, the more reduced forms of the acid (A-20 and A-24) and amide (A-11) had substantially less activity on FAAH. Converting the benzoic acid to a phenol (A-21) increased potency while the anisole (A-22) was completely inactive. Since the amide and acid appeared to be active, the amide bioisostere oxadiazole (A-25) was tested and had 38-fold less potency than the initial compound.
Since the substrates for FAAH tend to be relatively hydrophobic lipids, we speculated that conversion of the acid and primary amide to the corresponding esters or substituted amides would result in improved potency. The methyl ester (A-12) had 4-fold improved potency relative to the acid. Improving the bulk of the ester with an isopropyl group (A-13) results in a 11-fold loss in potency relative to the methyl ester. However, the similar potency of the benzyl ester (A-14) to the methyl ester demonstrates the bulk but not the size affects potency. Reversing the orientation of the ester (A-23) reduces the potency 3.4-fold. Relative to the primary amide, the methyl (A-18), ethanol (A-15) and glycyl (A-16) amides were all slightly less potent; however, the benzyl amide (A-27) was substantially less potent (16-fold). Generating the methyl ester of the glycyl amide (A-17) increased the potency 4-fold compared to the corresponding acid.
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Acids
Adamantane
Aldehydes
Amides
anisole
Benzoic Acid
Butanes
Cyclohexane
Dietary Fiber
Enzymes
Esters
Ethanol
inhibitors
Lipids
Nitriles
Nitrogen
Oxadiazoles
Phenol
piperidine
Psychological Inhibition
SOCS2 protein, human
Urea
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More about "Esters"
Esters are a diverse class of organic compounds formed by the reaction of an alcohol and an acid, resulting in the characteristic ester linkage.
They play a vital role in various fields, including chemistry, biology, and industry, with applications ranging from solvents and fragrances to plasticizers and pharmaceuticals.
The term 'ester' is derived from the German word 'Essigäther,' which means 'acetic ether.' Esters can be classified based on the type of alcohol and acid used in their formation.
Common examples include ethyl acetate, methyl benzoate, and glycerol triacetate.
These compounds exhibit a wide range of physical and chemical properties, such as varying melting and boiling points, solubility, and reactivity.
In the realm of biology, esters are crucial for various cellular processes.
Fatty acid esters, such as triacylglycerols (triglycerides), are the primary storage form of energy in many organisms.
Additionally, esters like cholesterol esters and phospholipids are important structural components of cell membranes.
Esters have a wide range of industrial applications.
They are commonly used as solvents, plasticizers, and flavoring agents in the food and fragrance industries.
Esters are also important in the production of paints, coatings, and adhesives, as well as in the synthesis of pharmaceuticals and other fine chemicals.
Analytical techniques, such as gas chromatography (GC) and high-performance liquid chromatography (HPLC), are commonly used to separate, identify, and quantify esters in complex mixtures.
Fluorescent probes, such as CFSE and CM-H2DCFDA, can be used to label and track esters in biological systems.
Additionally, DMSO and FBS are often used in cell culture media to maintain the stability and viability of ester-containing compounds.
In summary, esters are a versatile class of organic compounds with numerous applications in chemistry, biology, and industry.
PubCompare.ai's cutting-edge platform provides a seamless integration of intelligent protocol comparisons and powerful research tools to enhance the reproducibility and optimization of experiments involving esters and related compounds.
They play a vital role in various fields, including chemistry, biology, and industry, with applications ranging from solvents and fragrances to plasticizers and pharmaceuticals.
The term 'ester' is derived from the German word 'Essigäther,' which means 'acetic ether.' Esters can be classified based on the type of alcohol and acid used in their formation.
Common examples include ethyl acetate, methyl benzoate, and glycerol triacetate.
These compounds exhibit a wide range of physical and chemical properties, such as varying melting and boiling points, solubility, and reactivity.
In the realm of biology, esters are crucial for various cellular processes.
Fatty acid esters, such as triacylglycerols (triglycerides), are the primary storage form of energy in many organisms.
Additionally, esters like cholesterol esters and phospholipids are important structural components of cell membranes.
Esters have a wide range of industrial applications.
They are commonly used as solvents, plasticizers, and flavoring agents in the food and fragrance industries.
Esters are also important in the production of paints, coatings, and adhesives, as well as in the synthesis of pharmaceuticals and other fine chemicals.
Analytical techniques, such as gas chromatography (GC) and high-performance liquid chromatography (HPLC), are commonly used to separate, identify, and quantify esters in complex mixtures.
Fluorescent probes, such as CFSE and CM-H2DCFDA, can be used to label and track esters in biological systems.
Additionally, DMSO and FBS are often used in cell culture media to maintain the stability and viability of ester-containing compounds.
In summary, esters are a versatile class of organic compounds with numerous applications in chemistry, biology, and industry.
PubCompare.ai's cutting-edge platform provides a seamless integration of intelligent protocol comparisons and powerful research tools to enhance the reproducibility and optimization of experiments involving esters and related compounds.