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Chiralpak AD

Chiralpak AD is a chiral stationary phase used in high-performance liquid chromatography (HPLC) and other chromatographic techniques for the separation and analysis of enanatomeric compounds.
It is composed of amylose derivatized with 3,5-dimethylphenylcarbamate, which provides a unique chiral environment for the resolution of a wide range of racemic mixtures.
Chiralpak AD is a versatile tool in the field of asymmetric synthesis and pharmaceutical research, enabling the efficient and accurate determination of enantiomeric purity.
This MeSH term provides a concise overview of the key features and applications of Chiralpak AD, a widely used chiral stationary phase in analytical and preparative chromatography.

Most cited protocols related to «Chiralpak AD»

All samples for LC-MS-MS analysis were extracted on SPE columns as in Ref. 41 . Prior to extraction, 500 pg of deuterium-labeled internal standards d8-5S-HETE, d4-LTB4, d5LXA4 and d4PGE2 were added to facilitate quantification of sample recovery.
The LC-MS-MS system, QTrap 5500 (ABSciex), was equipped with an Agilent HP1100 binary pump and diode-array detector (DAD). An Agilent Eclipse Plus C18 column (100 mm × 4.6 mm × 1.8 μm) was used with a gradient of methanol/water/acetic acid of 60:40:0.01 (v/v/v) to 100:0:0.01 at 0.4 ml/min flow rate. To monitor and quantify the levels of the various LM, a multiple reaction monitoring (MRM) method was developed with signature ion fragments for each molecule. Identification was conducted using published criteria17 (link) with at least six diagnostic ions. Calibration curves were obtained using synthetic LM mixture (d8-5S-HETE, d4LTB4, d5LXA4, d4PGE2, TXB2, PGD2, PGF, RvD1, RvD2, RvD5, Protectin (PD)1, Maresin 1 (MaR1), 17-hydroxydocosahexaenoic acid (17-HDHA), 14-hydroxydocosahexaenoic acid (14-HDHA) and 7-hydroxydocosahexaenoic acid (7-HDHA) at 1, 10, 100, 275 pg. Linear calibration curves for each were obtained with r2 values in the range 0.98–0.99. Quantification was carried out based on peak area of the Multiple Reaction Monitoring (MRM) transition and the linear calibration curve for each compound. Where calibration curves for a structurally related DHA-derived product were not available (14,21-diHDPA, 13,14-diHDPA and 16,17-diHDPA), levels were monitored using a compound with similar physical properties.
For chiral lipidomic analysis, a Chiralpak AD-RH column (150 mm × 2.1 mm × 5 μm) was used with isocratic methanol/water/acetic acid 95:5:0.01 (v/v/v) at 0.15 ml/min. To monitor isobaric monohydroxy docosapentaenoic acid levels, a multiple reaction monitoring (MRM) method was developed using signature ion fragments for each molecule.
Publication 2013
7,14-dihydroxydocosa-4,8,10,12,16,19-hexaenoic acid 11-dehydrocorticosterone 14-hydroxydocosahexaenoic acid 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid Acetic Acid Acids CD59 Antigen Chiralpak AD Deuterium Diagnosis Dinoprost docosapentaenoic acid Hydroxyeicosatetraenoic Acids Leukotriene B4 Methanol Physical Processes Prostaglandin D2 Tandem Mass Spectrometry Thromboxane B2

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Publication 2012
acetonitrile Centrifugation Chiralpak AD Ethanol High-Performance Liquid Chromatographies MM-005 omega-Chloroacetophenone
Gradifloracin 16 (10.0 mg, 0.020 mmol) and indene 9b (23.3 μL, 0.20 mmol) in mesitylene were irradiated in microwave reactor at 170 °C for 15 min. Following the general procedure the obtained crude mixture was purified by silica gel chromatography (hexanes/EtOAc=10:1 to 8:1) to afford product 21 (11.8 mg, 80%) as a light yellow oil. Rf = 0.38 (hexanes/EtOAc, 3:1). IR (thin film) νmax: 3443, 2917, 2849, 1726, 1692, 1272 cm−1; 1H NMR (CDCl3, 400 MHz): δ 8.08 (dd, J = 8.4, 1.2 Hz, 2H), 7.60–7.56 (m, 1H), 7.45 (dd, J = 8.4, 8.4 Hz, 2H), 7.19–7.13 (m, 3H), 7.12–7.09 (m, 1H), 6.35 (dd, J = 7.2, 7.2 Hz, 1H), 5.94 (dd, J = 7.2, 7.2 Hz, 1H), 4.45 (d, J = 12.0 Hz, 1H), 4.28 (d, J = 12.0 Hz, 1H), 3.83 (dd, J = 9.2, 2.0 Hz, 1H), 3.57 (ddd, J = 6.4, 2.8, 1.2 Hz, 1H), 3.50–3.43 (m, 1H), 3.29 (ddd, J = 6.4, 2.8, 1.2 Hz, 1H), 3.23 (dd, J = 16.8, 10.4 Hz, 1H), 3.13 (s, 1H), 2.69 (dd, J = 16.8, 4.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz): δ 209.9, 166.6, 144.3, 142.4, 133.3, 133.2, 129.8 (two carbons ovrlp), 129.6, 128.6, 128.5 (two carbons ovrlp), 127.3, 126.7, 124.4, 124.0, 74.3, 68.4, 53.1, 50.1, 45.4, 37.7, 33.9; HRMS–ESI (m/z): [M + Na]+ calcd for C23H20NaO4, 383.1259; found, 383.1252. [α]22D = −22.3° (c = 0.24, CHCl3). The ee for 21 (24%) was determined using a Waters Breeze HPLC System (ChiralPak AD-H, 150 × 4.6 mm, 10% isopropanol in hexane, 1.0 mL/min, retention time 12.3 min (minor enantiomer) and 14.6 min (major enantiomer)) using UV detection at 254 nm.
Publication 2011
1H NMR Carbon Carbon-13 Magnetic Resonance Spectroscopy Chiralpak AD Chloroform Chromatography Gel Chromatography Hexanes High-Performance Liquid Chromatographies indene Isopropyl Alcohol Light mesitylene Microwaves n-hexane Retention (Psychology) Silica Gel Silicon Dioxide
Unless otherwise noted, all reagents and solvents were purchased from commercial sources and used without further purification. All reactions were performed under nitrogen atmosphere unless otherwise noted. The NMR spectra were obtained using a 400 or 500 MHz spectrometer. All 1H NMR spectra are reported in δ units ppm and are referenced to tetramethylsilane (TMS) if conducted in CDCl3 or to the central line of the quintet at 2.49 ppm for samples in d6-DMSO. All chemical shift values are also reported with multiplicity, coupling constants and proton count. All 13C NMR spectra are reported in δ units ppm and are referenced to the central line of the triplet at 77.23 ppm if conducted in CDCl3 or to the central line of the septet at 39.5 ppm for samples in d6-DMSO. Coupling constants (J values) are reported in hertz. Column chromatography was carried out on SILICYCLE SiliaFlash silica gel F60 (40–63 μm, mesh 230–400). High-resolution mass spectra were obtained using a SX-102A mass spectrometer (JEOL USA, Inc., Peabody, MA), a LCT mass spectrometer (Micromass Inc., Beverly, MA) or a Q-tof Ultima API mass spectrometer. All melting points were taken in glass capillary tubes on a Mel-Temp® apparatus and are uncorrected. All test compounds had a purity ≥ 95% as determined by either elemental analysis or high performance liquid chromatography (HPLC) analysis, unless otherwise noted. The elemental composition of compounds agreed to within ± 0.4% of the calculated values. Chemical and enantiomeric purities were determined using high performance liquid chromatography (HPLC) analysis on a Hewlett-Packard 1100 Series instrument equipped with a quaternary pump and a Daicel Chiralpak AD column (250 × 4.6 mm). UV absorption was monitored at λ = 254 nm. The injection volume was 1 μL. HPLC gradient was 50 % n-hexane and 50 % i-propanol with a flow rate of 1.0 mL/min. In some cases, chemical purity was determined using a Agilent 1100 HPLC instrument equipped with a quaternary pump and a Zorbax® SB-C8 column (30 × 4.6 mm, 3.5 μm). UV absorption was monitored at λ = 254 nm. The injection volume was 5 μL. HPLC gradient went from 5 % acetonitrile and 95 % water to 95 % acetonitrile and 5 % water (both solvents contain 0.1% trifluoroacetic acid) over 1.9 min with a total run time of 2.5 min and a flow rate of 3.0 mL/min.
Publication 2009
1-Propanol 1H NMR acetonitrile Atmosphere Capillaries Carbon-13 Magnetic Resonance Spectroscopy Chiralpak AD Chromatography Hexanes High-Performance Liquid Chromatographies Mass Spectrometry Nitrogen Protons Silica Gel Solvents Sulfoxide, Dimethyl tetramethylsilane Trifluoroacetic Acid Triplets Venous Catheter, Central
Reaction products of the two LOX enzymes and mutants with [1-14C]linoleic acid or [1-14C]arachidonic acid were analyzed on an Agilent 1100 HPLC equipped with a diode array detector connected online to a Radiomatic FLO-ONE A-100 radioactive detector. Straight-phase HPLC analysis used a Beckman Ultrasphere silica column (25 × 0.46 cm) eluted at a flow rate of 1 ml/min with hexane/isopropanol/acetic acid (100/2/0.1, by volume) with UV detection at 205, 220, 235 and 270 nm. Reversed-phase HPLC used a Waters Symmetry C18 5-μm column eluted at 1 ml/min with a solvent of methanol/water/acetic acid (80/20/0.01, by volume), and finally with methanol to elute unreacted substrate. Chiral analysis was performed on HODE methyl esters using a Daicel Chiralpak AD column (25 × 0.46 cm) eluted with hexane/methanol (100/2, by volume) at a flow rate of 1 ml/min, with UV detection at 235 nm [15 (link)].
Publication 2008
Acetic Acid Arachidonic Acid Chiralpak AD Enzymes Esters High-Performance Liquid Chromatographies Isopropyl Alcohol Linoleic Acid Methanol n-hexane Radioactivity Silicon Dioxide Solvents

Most recents protocols related to «Chiralpak AD»

Example 45

Conditions disclosed in table below can be used to separate stereoisomers of the racemic compound as shown:

Comp.
NoStructure and NameSeparation conditions
32[Figure (not displayed)]
Instrument: MG II preparative SFC(SFC-14) Column: ChiralPak AD, 250 × 30 mm I.D., 10 μm Mobile phase: A for CO2 and B for Ethanol(0.1% NH3H2O) Gradient: B 40% Flow rate: 80 mL/min Back pressure: 100 bar Column temperature: 38° C. Wavelength: 220 nm Cycle time: ~6.8 min
136[Figure (not displayed)]
Instrument: MG II preparative SFC(SFC-14) Column: ChiralPak AD, 250 × 30 mm I.D., 10 μm Mobile phase: A for CO2 and B for Ethanol Gradient: B 50% Flow rate: 80 mL/min Back pressure: 100 bar Column temperature: 38° C. Wavelength: 220 nm Cycle time: ~11 min

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Patent 2024
Chiralpak AD COMP protocol Ethanol Pressure Stereoisomers
UV spectra were obtained by using a Double Beam Spectrophotometer UH5300 (Hitachi High-Technologies, Tokyo, Japan). IR spectra were obtained on a Shimadzu Fourier Transform Infrared spectrometer using KBr pellets. NMR spectra were recorded with a Bruker Avance III 600 MHz spectrometer (Bruker, Karlsruhe, Germany). Optical rotations were measured on a Rudolph Autopol IV polarimeter (Hackettstown, NJ, USA). HRESIMS were measured on an Agilent (Santa Clara, CA, USA) 6200 Q-TOF MS system. Circular dichroism (CD) spectra were measured with an Applied Photophysics spectrometer (Chirascan, New Haven, CT, USA). HPLC was performed on an Agilent 1260 liquid chromatography system equipped with Zorbax (Santa Clara, CA, USA) SB-C18 columns (5 μm, 9.4 mm × 150 mm or 21.2 mm × 150 mm). Sephadex LH-20 (GE Healthcare, Chicago, IL, USA), Silica gel (200–300 mesh), and RP-18 gel (20–45 μm, FuJi, Tokyo, Japan) were used for column chromatography (CC). Chiral separation was carried out on a Chiralpak AD-H chiral column (5 μm, 250 × 4.6 mm; Daicel, Osaka, Japan).
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Publication 2023
Chiralpak AD Chromatography Circular Dichroism High-Performance Liquid Chromatographies Infrared Spectrophotometry Liquid Chromatography Optical Rotation Pellets, Drug sephadex LH 20 Silica Gel

10B-labeled BPA (10B-BPA, abbreviated as BPA in the text) was provided by Professor Weiqiang Chen (Institute of Modern Physics and Key Laboratory of Heavy Ion Radiation Biology and Medicine, Chinese Academy of Sciences, Lanzhou, China). Other synthetic materials and solvents are purchased from Innochem, Beijing, China. Cell counting kit-8 (CCK-8) was obtained from Dojindo Molecular Technologies, RPMI 1640 Medium, DMEN Medium, trypsin-EDTA (0.05%) and Fetal bovine serum (FBS) were purchased from Gibco™. In the liquid chromatography experiment, column: Chiralpak AD-RH 150 * 4.6mm I.D., 5um.
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Publication 2023
Chinese Chiralpak AD Edetic Acid Fetal Bovine Serum Heavy Ions Liquid Chromatography Pharmaceutical Preparations Solvents Trypsin
Aqueous K3PO4 or other base (2 M, 2 equivalents, 0.1 mL) was added to a mixture of β-keto ester 9 (0.1 mmol, 24.4 mg, ω = 95%) and organocatalyst IIX (2 mol%) in toluene or in CH2Cl2 (2 mL) under argon atmosphere. The mixture was cooled to −10℃ and NFSI (1.1 equivalents, 34.7 mg) was added in two portions over 2 h. The reaction mixture was stirred for another 12 h at −10 °C. After completion, the reaction was quenched by addition of NH4Cl (aq. sat, 4 mL) and extracted with CH2Cl2 (10 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and the volatiles were evaporated in vacuo. The residue was purified by column chromatography (Silica gel 60, EtOAc/n-Heptane = 1:15). Enantiomeric excess (ee) was determined by HPLC (Chiralpak AD-H, n-Hexane/i-PrOH = 200:1, flow rate 0.75 mL/min, λ = 250 nm, 10 °C) after isolation by column chromatography.
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Publication 2023
Argon Atmosphere Chiralpak AD Chromatography Esters Heptane High-Performance Liquid Chromatographies isolation Ketogenic Diet n-hexane Silica Gel Toluene
Solvents for extractions and chromatography were of technical grade and were distilled prior to use. Extracts were dried over technical-grade anhydrous Na2SO4. Melting points were determined on a Kofler micro hot stage. The NMR spectra were obtained on a Bruker Avance DPX 300 and Bruker Avance III 300 at 300 MHz for 1H nucleus, Bruker UltraShield 500 plus (Bruker, Billerica, MA, USA) at 500 MHz for 1H and 126 MHz for 13C nucleus, and Bruker Ascend 600 (Bruker, Billerica, MA, USA) at 600 MHz for 1H and 151 MHz for 13C nucleus, using DMSO-d6 and CDCl3, with TMS as the internal standard, as solvents. Mass spectra were recorded on an Agilent 6224 Accurate Mass TOF LC/MS (Agilent Technologies, Santa Clara, CA, USA), and IR spectra on a Perkin-Elmer Spectrum BX FTIR spectrophotometer (PerkinElmer, Waltham, MA, USA). CD spectra were recorded on a J-1500 Circular Dichroism Spectrophotometer (JASCO corporation, Tokyo, Japan). Column chromatography (CC) was performed on silica gel (Silica gel 60, particle size: 0.035–0.070 mm (Sigma-Aldrich, St. Louis, MI, USA)). HPLC analyses were performed on an Agilent 1260 Infinity LC (Agilent Technologies, Santa Clara, CA, USA) and Dionex Summit HPLC system (Dionex Corporation, Sunnyvale, CA, USA) using CHIRALPAK AD-H (0.46 cm ø × 25 cm) and CHIRALPAK OJ-H (0.46 cm ø × 25 cm), as the chiral columns (Chiral Technologies, Inc., West Chester, PA, United States). All the commercially available chemicals used were purchased from Sigma-Aldrich (St. Louis, MI, USA). In addition, (1S,2S,4R)-7,7-dimethyl-1-(pyrrolidin-1-ylmethyl)bicyclo[2.2.1]heptan-2-amine (1b) was prepared following the literature procedure [30 (link)].
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Publication 2023
Amines Cell Nucleus Chiralpak AD Chromatography Circular Dichroism High-Performance Liquid Chromatographies Infrared Spectrophotometry Mass Spectrometry Silica Gel Solvents Spectroscopy, Fourier Transform Infrared Sulfoxide, Dimethyl

Top products related to «Chiralpak AD»

Sourced in Japan
The Chiralpak AD-H column is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of chiral compounds. It utilizes a stationary phase consisting of amylose derivatized with 3,5-dimethylphenylcarbamate, which provides effective enantioseparation of a wide range of chiral analytes.
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Chiralpak AD is a chiral stationary phase used in high-performance liquid chromatography (HPLC) for the separation and analysis of enantiomers. It is composed of amylose tris(3,5-dimethylphenylcarbamate) coated on a silica gel support.
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The JNM-ECA500 is a high-performance nuclear magnetic resonance (NMR) spectrometer designed for analytical and research applications. It provides a stable and reliable platform for the acquisition of NMR data, featuring a wide range of functionality and capabilities.
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Chiralpak AD-H is a high-performance liquid chromatography (HPLC) column used for the separation and analysis of chiral compounds. It is designed to provide efficient and selective separation of enantiomers, which are mirror-image molecules that have the same chemical formula but different three-dimensional structures. The Chiralpak AD-H column utilizes a polysaccharide-based chiral stationary phase to achieve this separation.
The Varian ProStar 335 LC Detector is a high-performance liquid chromatography (HPLC) detector designed to provide reliable and accurate analysis of a wide range of samples. The core function of this detector is to measure the absorption of light by the components of a liquid sample as it flows through the detector cell, allowing for the identification and quantification of the analytes present. The ProStar 335 offers a robust and versatile solution for HPLC applications across various industries.
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The Lux Cellulose-4 is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of a wide range of chiral compounds. It features a cellulose-based stationary phase that provides efficient and selective separation of enantiomers.
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The Agilent 1200 series is a modular high-performance liquid chromatography (HPLC) system. It is designed to provide reliable and efficient separation and analysis of a wide range of samples. The system is composed of various components, including pumps, autosamplers, detectors, and a column compartment, which can be configured to meet specific analytical requirements.
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The Chiralpak AD‐RH column is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of chiral compounds. It utilizes a stationary phase that is coated with a chiral selector, allowing for the efficient separation of enantiomers. The column is suitable for reversed-phase chromatography applications.
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The Polaris C18-A is a high-performance liquid chromatography (HPLC) column designed for the separation and analysis of a wide range of organic compounds. It features a spherical silica-based stationary phase with a C18 alkyl bonded ligand, providing effective separation and retention of both polar and non-polar analytes.
The ChiralPakAD column is a high-performance liquid chromatography (HPLC) column used for the separation and analysis of chiral compounds. It utilizes a cellulose-based stationary phase to provide efficient enantioseparation of a wide range of racemic mixtures.

More about "Chiralpak AD"

Chiralpak AD is a versatile chiral stationary phase (CSP) widely used in high-performance liquid chromatography (HPLC) and other chromatographic techniques for the separation and analysis of enantiomeric compounds.
This amylose-based CSP, which features 3,5-dimethylphenylcarbamate derivatization, provides a unique chiral environment that enables the efficient resolution of a wide range of racemic mixtures.
Chiralpak AD and its variants, such as Chiralpak AD-H and Chiralpak AD-RH, are essential tools in the fields of asymmetric synthesis and pharmaceutical research.
These columns allow for the accurate determination of enantiomeric purity, a crucial step in the development and quality control of chiral drug substances and other enantiomerically pure compounds.
The versatility of Chiralpak AD is further enhanced by its compatibility with a variety of HPLC systems, including the Agilent 1200 series and Varian ProStar 335 LC detectors.
Researchers can also utilize the Lux Cellulose-4 and Polaris C18-A columns for complementary separation techniques.
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This data-driven approach helps identify the best protocols and products for reproducible research, streamlining the discovery and optimization of chiral separations.
Whether you're working in asymmetric synthesis, pharmaceutical development, or other fields requiring enantiomeric analysis, Chiralpak AD and its related products offer a powerful solution for your chiral separation needs.
Explore the capabilities of this widely used chiral stationary phase and leverage the insights provided by PubCompare.ai to enhance your research efficiency and reproducibility.