The NMR spectra were measured with Agilent 400 MR DDR2 (Agilent Technologies Inc., United States) using CDCl3 (Merck KGaA, Germany) as a solvent and referenced on residual CDCl3 signal (1H δ 7.26 ppm). The spectra of corresponding epimers were identical to NMR spectra published by Russo et al.11 (link).
Cdcl3
Manufactured by Merck Group
Sourced in United States, Germany, United Kingdom, Italy, India, France, Poland, Sao Tome and Principe
CDCl3 is a common laboratory solvent used for nuclear magnetic resonance (NMR) spectroscopy. It is a colorless, dense liquid with a characteristic chloroform-like odor. CDCl3 is a versatile solvent that can dissolve a wide range of organic compounds, making it a valuable tool for various chemical analyses and research applications.
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Lab products found in correlation
Dmso d6, by Merck Group (27 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (13 mentions)
Cd3od, by Merck Group (10 mentions)
Sephadex lh 20, by Merck Group (9 mentions)
Acetonitrile, by Merck Group (7 mentions)
Silica gel, by Merck Group (7 mentions)
Silica gel 60 pf254, by Merck Group (6 mentions)
Methanol, by Merck Group (6 mentions)
Silica gel 60, by Merck Group (6 mentions)
Tetrahydrofuran, by Merck Group (5 mentions)
Toluene, by Merck Group (5 mentions)
N hexane, by Merck Group (4 mentions)
Acetone d6, by Merck Group (4 mentions)
Diethyl ether, by Merck Group (4 mentions)
Dichloromethane, by Merck Group (4 mentions)
Ethanol, by Merck Group (4 mentions)
N dodecane, by Merck Group (4 mentions)
Toluene, by Thermo Fisher Scientific (4 mentions)
N n dimethylformamide (dmf), by Merck Group (4 mentions)
Silica gel 60 f254 plate, by Merck Group (3 mentions)
188 protocols using cdcl3
1
NMR Spectra Analysis of Epimers
2
Synthesis and Characterization of Dodecyl Prodrugs
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Dodecyl prodrug/drug analogue was used as synthesised by previous publication. Brij S10, Brij S20, Brij S100, tetrahydrofuran and deuterated solvents (CDCl3 and D2O) were all purchased from Sigma Aldrich and used as received apart from CDCl3 where 0.1% tetramethylsilane was added. Lipoid S100 was purchased from Lipoid and used as received. Tricaprin was purchased from Tokyo chemical industry and used as received. Dynasan 114 (trimyrisitn) and Dynasan 118 (tristearin) was kindly gifted from IOI Oleochemical, Hamburg. Lamivudine was purchased from Top Well Medipharma Group.
3
Spectroscopic Characterization of Organic Compounds
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1H (500 MHz) and 13C (125 MHz) nuclear magnetic resonance (NMR) spectra were measured on a Bruker spectrometer (USA), using CDCl3 as solvent and TMS as internal standard (Merck, Germany). Mass spectra were obtained using a Hewlett-Packard 7890A mass spectrometer (USA). Infrared spectra were also recorded using an FTIR spectrometer (WQF-510, Rayleigh, China). Open column chromatography was performed using silica gel (70–230 mesh) and analytical grade solvents (Merck, Germany). Separations were monitored by thin layer chromatography on Merck 60 F254 (0.25 mm) plates and were visualized by UV inspection (Camag, Switzerland) and/or staining with Cerium Sulphate/molibdate (Merck, Germany) proceeding by heating.
4
Spectral Analysis and Purification of Organic Compounds
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The 1H (400 MHz) and 13C (100 MHz) NMR spectra were taken on a Bruker Advance 400 spectrometer (Bruker Corporation, Billerica, MA, USA), using deuterated chloroform (CDCl3, Merck, Darmstadt, Germany); chemical shifts of both the hydrogen and carbon spectrum are found in δ (ppm) and coupling constants (J) in Hz. The analytical reactive grade solvents used for the extractions, isolations, and purification of the compounds were hexane (Merck, Darmstadt, Germany), ethyl acetate (EtOAc, Merck, Darmstadt, Germany) and methanol (MeOH, Merck, Darmstadt, Germany). The separation was carried out by column chromatography (CC) with the stationary phase of silica gel 60 (230–450, Alfa Aesar, Switzerland) and silica gel coated plates were used (ALUGRAM® SIL G/UV254, 0.20 mm, MACHEREY-NAGEL, Duren, Germany) for thin-layer chromatography (TLC) analysis.
5
Analytical Methods for Chemical Characterization
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CD3OD, CDCl3, and DMSO-d6 (HPLC grade) were obtained from Merck (Darmstadt, Germany). HPLC-grade methanol (Merck) and phosphoric acid (Hengxing Chemical Reagent Co., Ltd, Tianjin, China) were used for HPLC analysis. CCK-8 was obtained from Qihai Biological Technology Ltd (Shanghai, China). All other solvents used in this study, such as acetone, petroleum ether (PE), dichloromethane (CH2Cl2), ethyl acetate (EtOAc), ethanol, and methanol were of analytical grade and supplied by Hengxing Chemical Reagent Co., Ltd.
6
Prasiola crispa Sterols Characterization
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An aliquot of Prasiola crispa n-hexane extract (10 mg) was analyzed by NMR spectra (proton and carbon) on Varian-Unity Plus 300 MHz spectrometer, employing CDCl3 (99.8%, Merck, Whitehouse Station, NJ, USA), as a solventand TMS as internal standard. Chemical shifts were reported inδ(ppm) and coupling constants (J), in Hz. Multiplicities of 13C signals were obtained by APT. All solvents were of HPLC grade for extraction, fractionation and isolation of the sterols.TLC separations were carried out on Merck silica gel 60F-254 (0.2 mm) percolated aluminum plates. Once developed, the plates were visualized by spraying them with 2% ceric sulfate in sulfuric acid, followed by gentle heating. Fractionation was monitored by thin layer chromatography. Silica gel60 (Merck, 70–230 and 230–400 mesh), was used for column chromatography.
The hexanic extract was fractionated by column chromatographies on silica gel Merck 70–230 and 230–400 mesh, using hexane/CH2Cl2/ethyl acetate as eluent (F1–F30). All fractions were abundant in sterols. The most abundant steroidal components were detected by NMR spectra (campesterol, β-sitosterol, and stigmasterol). The identification was based on NMR comparisons with standards (Sigma/Aldrich Products) and/or literature [54 (link)] (Table 1 ).
The hexanic extract was fractionated by column chromatographies on silica gel Merck 70–230 and 230–400 mesh, using hexane/CH2Cl2/ethyl acetate as eluent (F1–F30). All fractions were abundant in sterols. The most abundant steroidal components were detected by NMR spectra (campesterol, β-sitosterol, and stigmasterol). The identification was based on NMR comparisons with standards (Sigma/Aldrich Products) and/or literature [54 (link)] (
7
Synthesis of Well-Defined Copolymers
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Lauryl methacrylate (LMA, 96%), benzyl methacrylate
(BzMA, 96%), cumyl dithiobenzoate (CDB), and CDCl3 were
purchased from Merck (UK). Each monomer was passed through basic alumina
in order to remove the inhibitor prior to use. tert-Butyl peroxy-2-ethylhexanoate (Trigonox 21S or T21s) initiator was
supplied by AkzoNobel (The Netherlands). Glycerol, sodium iodide (NaI),
and tetrahydrofuran (THF) were purchased from VWR (UK). Group III
hydroisomerized mineral oil (viscosity = 3.1 cSt at 100 °C; refractive
index = 1.462) was kindly provided by The Lubrizol Corporation Ltd.
(Hazelwood, Derbyshire, UK). Deionized water was used for all experiments.
(BzMA, 96%), cumyl dithiobenzoate (CDB), and CDCl3 were
purchased from Merck (UK). Each monomer was passed through basic alumina
in order to remove the inhibitor prior to use. tert-Butyl peroxy-2-ethylhexanoate (Trigonox 21S or T21s) initiator was
supplied by AkzoNobel (The Netherlands). Glycerol, sodium iodide (NaI),
and tetrahydrofuran (THF) were purchased from VWR (UK). Group III
hydroisomerized mineral oil (viscosity = 3.1 cSt at 100 °C; refractive
index = 1.462) was kindly provided by The Lubrizol Corporation Ltd.
(Hazelwood, Derbyshire, UK). Deionized water was used for all experiments.
8
Synthesis of Polycaprolactone via Alcoholysis
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All manipulations were carried out using the standard Schlenk techniques under an atmosphere of argon. ε-Caprolactone (CL, Acros, 99%, Saint Louis, MO, USA) and benzyl alcohol (BnOH, Sigma-Aldrich, 99.8%, Saint Louis, MO, USA) were dried over CaH2, distilled from CaH2 under reduced pressure and stored under argon. The catalyst (HPCP) was synthesized according to previously reported work [56 (link)], was washed with 0.1 M NaOH and distilled water and purified by dialysis. Finally, it was dried in vacuum at 50 °C overnight. Deuterated solvent CDCl3 (99.8%, for spectroscopy, Merck, Darmstadt, Germany), CH2Cl2 (Sigma-Aldrich, >99.5%, USA), tetrahydrofuran (LiChrosolv®, Merck, Darmstadt, Germany, >99.9%) were used as received.
9
Synthesis of Organic Compounds
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Reagents and solvents were purchased from several commercial suppliers. TBTU, N,O-dimethylhydroxylamine hydrochloride, TFA, and Cbz-amino acids were obtained from Fluorochem. N-Methyl morpholine were purchased from VWR. TFA, LiAlH4, methyl (triphenylphosphoranylidene) acetate, and methyl (triphenylphosphoranylidene)-2-propanone were obtained from Merck, as well as silica gel 60 F254 plates and silica gel (200–400 mesh) employed for TLC and column chromatography, respectively. All the TLC were treated with an ethanol solution of phosphomolybdic acid hydrate (15%), which was obtained by Fluorochem, meanwhile, TLC in which aldehydes were evaluated, were treated with 2,4-dinitrophenylhydrazine TLC stain. All the 1H and 13C spectra were performed on a Varian 500 MHz, operating at 499.74 and 125.73 MHz for 1H and 13C, respectively. Deuterated solvents, namely CDCl3 and MeOD, were obtained from Merck and the signal of the solvents was used as the internal standard. Splitting patterns are described as singlet (s), doublet (d), doublet of doublet (dd), triplet (t), quartet (q), multiplet (m), and broad singlet (bs). Chemical shifts are expressed in ppm and coupling constants (J) in Hz. Elemental analyses were performed on a C. Erba model 1106 (elemental analyzer for C, H, and N) apparatus, and ±0.4% of the theoretical values were found.
10
Atractylodes Metabolite Identification
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Atractylodes standards, β-eudesmol, and atractylenolide III were obtained from Fujifilm Wako Pure Chemical Co. (Osaka, Japan). For NMR acquisition, CD3OD-d4 (99.8% D) and CDCl3 (99.8% D) were purchased from Merck KGaA (Darmstadt, Germany). The signals in the 1H NMR spectra of Atractylodes extracts were assigned to individual metabolites on the basis of thorough analyses of the 2D NMR spectra and spiking experiments. The PCR-grade tubes, tips, and most biological reagents used for DNA authentication were acquired from Qiagen (Valencia, CA, USA) and/or Thermo-Fisher Scientific and Beckman Coulter (Indianapolis, IN, USA). LO3 agarose for gel electrophoresis was purchased from Takara (Kyoto, Japan).
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