Csh c18

Manufactured by Waters Corporation

Sourced in United States

The CSH C18 is a high-performance liquid chromatography (HPLC) column produced by Waters Corporation. It is designed for the separation and analysis of a wide range of organic compounds. The column features a C18 stationary phase, which is a commonly used reversed-phase packing material. The core function of the CSH C18 column is to provide efficient separation and high-resolution analysis of various sample types.

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XSelect® CSH C18 (35 citations) Acquity UPLC CSH C18 (21 citations) ACQUITY UPLC® CSHTM C18 column (6 citations) Acquity CSH C18 1.7 μm 1 × 150 mm column (4 citations) XSelect CSH C18 2.5 um resin (4 citations) UPLC CSH C18 (4 citations) XSelect Peptide CSH C18 column (4 citations) CSH C18 1.7 μm, (3 citations) Acquity UPLC® M-Class CSHTM C18 column (2 citations) Acquity UPLC C18 CSH chromatographic column (2 citations)

32 protocols using csh c18

UPLC Analysis of Protein Digest Samples

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For comparison purposes, samples determined by XUPLC were additionally analyzed by a commercial UPLC system (Waters
nanoAcquity), with the system operated in a non-trapping format. Plumbing from the nanoAcquity injection valve (2 μl loop)
to the commercial UPLC column (CSH C18, 75 μm x 25 cm, 1.7 μm particles, Waters), was accomplished using FS tubing
with frit, 25 μm id x 360 od x 10″ (Waters, #430001570) from the injection value to a nano-tee
(#289002576, Waters) to which the column was attached. The injection loop was filled with 2 μL of sample then the
following solvent program was initiated using a flow rate of 0.30 μL/min. Time zero to 0.1 min, 3% MPB;
0.1–50 min, 3–35% MPB; 50–70 min, 35–95% MPB; 70–80 min, 95% MPB;
8–83 min, 95–3% MPB; 83–109 min, 3% MPB. The column was housed in a column heater device
held at 45 °C, with a sample mass of 0.20 μg injected (2 μL of 4.5 μM protein digest).

Mozziconacci O., Stobaugh J.T., Bommana R., Woods J., Franklin E., Jorgenson J.W., Forrest M.L., Schöneich C, & Stobaugh J.F. (2017). Profiling the Photochemical-Induced Degradation of Rat Growth Hormone with Extreme Ultra-pressure Chromatography-Mass Spectrometry Utilizing Meter-Long Microcapillary Columns Packed with Sub-2-μm Particles. Chromatographia, 80(9), 1299-1318.

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Preparative LCMS Purification of Compound 10500

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EXAMPLE 10500

[Figure (not displayed)]

Example 10500 was prepared following “General Synthetic Sequence A”. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 8-48% B over 30 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal vaporation. The material was further purified via preparative LC/MS with the following conditions: Column: Waters CSH C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 10-70% B over 15 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 20.0 mg, and its estimated purity by LCMS analysis was 91%.

Analysis condition C: Retention time=1.66 min; ESI-MS(+) m/z 944.3 (M+2H)

Analysis condition E: Retention time=1.40 min; ESI-MS(+) m/z 944.2 (M+2H).

US10358463B2. Immunomodulators (2019-07-23). BRISTOL-MYERS SQUIBB COMPANY [US]. Inventors: Michael Matthew Miller [US], Martin Patrick Allen [US], Ling Li [US], Michael S. Bowsher [US], Eric P. Gillis [US], Eric Mull [US], Qian Zhao [US], Li-Qiang Sun [US], David R. Langley [US], Paul Michael Scola [US].

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Lipid Profiling by LC-HRMS

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Following Bligh-Dyer extraction, the organic layers were dried and subsequently reconstituted in acetonitrile-isopropanol-water (ACN:IPA:H₂O 65:30:5, v/v/v). A 1200 infinity series^® high performance liquid chromatography (HPLC) system (Agilent Technologies, Santa Clara, CA, USA) coupled to an Exactive Orbitrap^® mass spectrometer (Thermo Fisher Scientific, Bremen, Germany) equipped with a heated electrospray (H-ESI II) source (operating in polarity switch mode) was used for lipid profiling. The full instrument calibration was performed using a MSCAL6 ProteoMassT LTQ/FT-Hybrid ESI Pos/Neg^® (Sigma–Aldrich, St. Louis, MO, USA). Xcalibur 2.2^® (Thermo Fisher Scientific, San Jose, CA, USA) was used for data acquisition and analysis. Lipid species separation was performed on a reverse phase CSH^® C₁₈ (100 × 2.1 mm² i.d., 1.7 µm particle size) column (Waters Corporation, Milford, MA, USA) using ACN:H₂O (60:40) and IPA:ACN:H₂O (88:10:2) as solvent A and B, respectively; both containing 10 mM ammonium acetate and 0.1% acetic acid [47 (link)]. The precision associated with sample preparation and LC-HRMS measurement was determined based on a quality control (QC) consisting of a pool of 10 mothers’ milk provided by the milk bank of Nantes Hospital Center. Summary assay procedures have been detailed in Supplementary Material.

Alexandre-Gouabau M.C., Moyon T., Cariou V., Antignac J.P., Qannari E.M., Croyal M., Soumah M., Guitton Y., David-Sochard A., Billard H., Legrand A., Boscher C., Darmaun D., Rozé J.C, & Boquien C.Y. (2018). Breast Milk Lipidome Is Associated with Early Growth Trajectory in Preterm Infants. Nutrients, 10(2), 164.

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Comprehensive Lipid Profiling Protocol

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For analyzing glycerolipids and glycerophospholipids, a linear ion trap–Orbitrap mass spectrometer (Orbitrap Elite; Thermo Fisher Scientific) was used and coupled online with an ultra-high-performance LC system (ACQUITY UPLC; Waters). Chromatographic separation was performed on a reverse-phase column (CSH C18, 1.8 µm, 2.1 × 100 mm; Waters) maintained at 65°C using mobile phase A (10 mM ammonium acetate, pH 5.0, and 40% acetonitrile) and mobile phase B (10 mM ammonium acetate, pH 5.0, and 10% acetonitrile in isopropyl alcohol) in a gradient program (0–10 min: 40–99.9% B; 10–12 min: 99.9% B; 12–13 min: 99.9–40% B; and 13–14 min: 40% B; linear gradient for all) with a flow rate of 500 µl/min. The mass spectrometer was operated in positive- and negative-ion modes and set to one full Fourier transform MS scan (m/z = 100–1,200, resolution = 30,000). The mass-to-charge ratio (m/z) of TAG and DAG species was searched as [M + NH₄]⁺ ions, PC and lysoPC species as [M + H]⁺ ions, and other classes of phospholipid, lysophospholipid, and free fatty acid species as [M-H]⁻ ions. The lipids were quantified with the Xcalibur software (Thermo Fisher Scientific) and analyzed with Excel (Microsoft). Data were normalized by either heptadecanoic acid (negative-ion mode) or d5-TG (positive-ion mode).

Huang L.J, & Chen R.H. (2022). Lipid saturation induces degradation of squalene epoxidase for sterol homeostasis and cell survival. Life Science Alliance, 6(1), e202201612.

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Metabolite Detection via High-Resolution Mass Spectrometry

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The detection was performed using a tandem Q Exactive high-resolution mass spectrometer (Thermo Fisher Scientific, USA). The chromatographic column used was a CSH C18 (1.7 μm, 2.1 × 100 mm, Waters, USA). In positive ionization mode, the mobile phases consisted of an aqueous solution containing 10 mM ammonia formate, 0.1% formic acid, and 60% acetonitrile (liquid A) and a solution containing 10 mM ammonia formate, 0.1% formic acid, 90% isopropanol, and 10% ACN (liquid B). Additionally, in negative ionization mode, an aqueous solution containing 10 mM ammonia formate and 60% ACN (liquid A) and a solution containing 10 mM ammonia formate, 90% isopropanol, and 10% acetonitrile were used.

Wei Y., Cai X., Wu Q., Liao H., Liang S., Fu H., Xiang Q, & Zhang S. (2023). Extraction, Isolation, and Component Analysis of Turmeric-Derived Exosome-like Nanoparticles. Bioengineering, 10(10), 1199.

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Preparative LC/MS Purification of Compound

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Example 9007

[Figure (not displayed)]

The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 methanol:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanol:water with 10-mM ammonium acetate; Gradient: 45-90% B over 30 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: Waters CSH C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 5-45% B over 30 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 19.3 mg, and its estimated purity by LCMS analysis was 100%.

Analysis condition A: Retention time=1.95 min; ESI-MS(+) m/z 907.8 (M+2H).

US09944678B2. Immunomodulators (2018-04-17). BRISTOL-MYERS SQUIBB COMPANY [US]. Inventors: Li-Qiang Sun [US], Qian Zhao [US], Eric P. Gillis [US], Michael Matthew Miller [US], Martin Patrick Allen [US], Eric Mull [US], Paul Michael Scola [US].

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Chromatographic Evaluation of UPLC Columns

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All chromatographic evaluations were performed using ACQUITY UPLC Classic, H‐Class, or I‐Class instruments equipped with ACQUITY photodiode array detectors (Waters, Milford, MA). ACQUITY UPLC BEH C₁₈, CSH C₁₈, HSS T3, and Atlantis PREMIER BEH C₁₈ AX columns (1.7 or 1.8, 2.5 and 5 μm, 2.1 × 50 mm) were obtained from Waters (Milford, MA).

Walter T.H., Alden B.A., Field J.A., Lawrence N.L., Osterman D.L., Patel A.V, & DeLoffi M.A. (2021). Characterization of a highly stable mixed‐mode reversed‐phase/weak anion‐exchange stationary phase based on hybrid organic/inorganic particles. Journal of Separation Science, 44(5), 1005-1014.

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Purification of Example 10002

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EXAMPLE 10002

[Figure (not displayed)]

Example 10002 was prepared following “General Synthetic Sequence A”. The crude material of Example 10002 was purified via preparative LC/MS with the following conditions: Analysis LCMS Condition C: Column: Waters BEH C18, 2.1×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 70° C.; Gradient: 0% B, 0-100% B over 3 minutes, then a 2.0-minute hold at 100% B; Flow: 0.75 mL/min; Detection: UV at 220 nm. Analysis LCMS Condition D: Column: Waters CSH C18, 2.1×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 acetonitrile: water with trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with trifluoroacetic acid; Temperature: 70° C.; Gradient: 0% B, 0-100% B over 3 minutes, then a 2.0-minute hold at 100% B; Flow: 0.75 mL/min; Detection: UV at 220 nm. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 22.6 mg, and its estimated purity by LCMS analysis was 98%.

Analysis condition C: Retention time=1.44 min; ESI-MS(+) m/z 945.30 (M+2H).

Analysis condition D: Retention time=1.15 min; ESI-MS(+) m/z 945.25 (M+2H).

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Preparative LC/MS Purification of Compound

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EXAMPLE 10502

[Figure (not displayed)]

Example 10502 was prepared following “General Synthetic Sequence A”. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 8-48% B over 30 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: Waters CSH C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 10-70% B over 15 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 1.4 mg, and its estimated purity by LCMS analysis was 94%.

Analysis condition C: Retention time=1.30 min; ESI-MS(+) m/z 916.2 (M+2H)

Analysis condition E: Retention time=1.16 min; ESI-MS(+) m/z 916.1 (M+2H.

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Purification of Example 10003 Compound

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EXAMPLE 10003

[Figure (not displayed)]

Example 10003 was prepared following “General Synthetic Sequence A”. The crude material of Example 10003 was purified via preparative LC/MS with the following conditions: Analysis LCMS Condition C: Column: Waters BEH C18, 2.1×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 70° C.; Gradient: 0% B, 0-100% B over 3 minutes, then a 2.0-minute hold at 100% B; Flow: 0.75 mL/min; Detection: UV at 220 nm. Analysis LCMS Condition D: Column: Waters CSH C18, 2.1×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 acetonitrile: water with trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with trifluoroacetic acid; Temperature: 70° C.; Gradient: 0% B, 0-100% B over 3 minutes, then a 2.0-minute hold at 100% B; Flow: 0.75 mL/min; Detection: UV at 220 nm. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 1.2 mg, and its estimated purity by LCMS analysis was 94%.

Analysis condition C: Retention time=1.48 min; ESI-MS(+) m/z 944.70 (M+2H).

Analysis condition D: Retention time=1.26 min; ESI-MS(+) m/z 944.45 (M+2H).

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