PLGA acid (PLGA-COOH;1.0 g, 0.170 mmol, Mn = 7000; Lactel), polyethylene glycol (HO-PEG-OH;2.29 g, 0.684 mmol, Mn = 2000; Sigma Aldrich), and deoxyadenosine monophosphate (dMAP; 0.023 g, 0.187 mmol; Alfa Aesar) were dissolved in 30 mL of anhydrous dichloromethane (CH2Cl2; Sigma Aldrich). Next, a 10 mL CH2Cl2 solution of dicyclohexylmethanediimine (DCC; 0.141 g or 0.684 mmol; Sigma Aldrich) was added dropwise to the reaction mixture at 0 °C with magnetic stirring. The mixture was warmed up to room temperature and stirred overnight. Insoluble dicyclohexylurea (C13H24N2O) was filtered out. The raw product was precipitated out by adding 50 mL of 50:50 diethyl ether ((C2H5)2O; Sigma Aldrich) and methanol (CH3OH; Sigma Aldrich) to the mixture. The mixture was centrifuged for 15 min at 4 °C. The purification step was repeated 4–5 times, followed by 1H NMR analysis that was performed on a Varian Mercury Plus 400 system.
Ch2cl2
Manufactured by Merck Group
Sourced in United States, Germany
CH2Cl2, commonly known as dichloromethane, is a colorless, volatile, and dense liquid chemical compound. It is used as an industrial solvent and as a process agent in various applications.
Automatically generated - may contain errors
Lab products found in correlation
N n dimethylformamide (dmf), by Merck Group (6 mentions)
Methanol, by Merck Group (5 mentions)
Acetone, by Merck Group (5 mentions)
K2co3, by Merck Group (4 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (4 mentions)
Ch3cn, by Merck Group (4 mentions)
Piperidine, by Merck Group (3 mentions)
Na2so4, by Merck Group (3 mentions)
Diethyl ether, by Merck Group (3 mentions)
Chcl3, by Merck Group (3 mentions)
Toluene, by Merck Group (3 mentions)
Cdcl3, by Merck Group (3 mentions)
Ch3oh, by Merck Group (3 mentions)
Milli q integral water purification system, by Merck Group (2 mentions)
Chloro decyl dimethylsilane, by Merck Group (2 mentions)
Microtof q instrument, by Bruker (2 mentions)
Avance 300, by Bruker (2 mentions)
Avance 500, by Bruker (2 mentions)
Etoac, by Merck Group (2 mentions)
Tyramine, by Merck Group (2 mentions)
55 protocols using ch2cl2
1
Synthesis of PLGA-PEG-dAMP Conjugate
2
Synthesis of Taxadien-5α-ol
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The synthesis of taxadien-5α-ol (2 ) is adapted from a previously described method30 (link). Tert-BuOOH (21.3 μL of 98% purity, 0.114 mmol; Sigma–Aldrich) was added to a solution of SeO2 (3.3 mg, 0.030 mmol; Strem) in CH2Cl2 (50 μL; Sigma–Aldrich) and stirred for 0.5 h. Subsequently, purified taxadiene (1 ) (15.5 mg, 0.0570 mmol) in CH2Cl2 (200 μL) was added to the solution and allowed to stir for 2.5 h at room temperature. The resulting yellow solution was concentrated on a rotary evaporator under reduced pressure to yield yellow crude oil. Flash chromatography was carried out using a 2 mL glass Pasteur pipette loaded with 200 mg of P60 silica gel (SiliCycle) with hexane (HPLC grade; VWR) as the initial mobile phase. The column was first eluded with 100% hexane to yield unreacted 1 (21% recovery), then with hexane-diethyl ether (Fischer Chemical) in a ratio of 5:1 to yield 2.3 mg of an over-oxidized ketone product (TLC Rf = 0.63 when eluded with hexane-Et2O 5:1 and stained with KMnO4; 14% isolated yield) and 1.8 mg of 2 (TLC Rf = 0.36 when eluded with hexane-Et2O 5:1 and stained with KMnO4; 11% isolated yield). Fractions were collected in 200 μL volume. The 1H NMR data of synthetic taxadien-5α-ol (2 ) are reported and compared to 2 heterologously produced in E. coli to confirm its identity (Supplementary Figs. 14 –15 ).
3
GC-MS Analysis of Organic Compounds
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Chromatographic studies were performed on a GC-MS chromatograph (SCION TQ, BRUKER). About 10.0 µL of the sample was dissolved in 2.0 mL of CH2Cl2 (Sigma-Aldrich) and 1.0 µL of the solution was injected onto the column. The chromatograph was equipped with a VF-5ms Crawford Scientific silica column. The electron energy was 70 eV, and the ion source was at 200 °C. Helium was used as the carrier gas at a flow rate 1.0 mL/min. Temperature program: Enable Coolant at 50.0 °C, Coolant Timeout 20.00 min, Stabilization Time 0.50 min; Temperature 60.0 °C, Hold 3.00 min., Total 3.00 min.; Temperature 280.0 °C, Rate 10.0 °C/min., Hold 35.00 min., Total 60.00 min. The identification of compounds was based on a comparison of their retention time as well as mass spectra with NIST standards.
4
Synthesis of Specialized Pro-resolving Lipid Mediators
5
GC-FID Analysis of Total Extracted Hydrocarbons
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The composition of the Total Extracted and Resolved Hydrocarbons and their
derivates (TERHCs) were analysed by high-resolution GC-FID (DANI Master
GC Fast Gas Chromatograph System, DANI Instruments Sp.A., Milan).
After acidification, TERHCs from samples were extracted at room temperature on a
shaking table by using dichloromethane (CH2Cl2,
Sigma-Aldrich, Milan; 10% v/v). This procedure was repeated three times, and the
CH2Cl2 phase was combined and treated with sodium
sulfate anhydrous (Na2SO4, Sigma-Aldrich, Milan) in order
to remove any residual water (Ehrhardt
et al., 1991 ; Wang et al., 1998 (link); Dutta and Harayama 2001 (link); Denaro
et al., 2005 ). Extracts were concentrated by
rotary evaporation (Rotavapor model R110; Büchi Labortechnik AG, Switzerland) at
room temperature (< 30 °C), followed by evaporation under a stream of
nitrogen and taken up into a solution containing heptamethyl-nonane as an
internal standard (79 μg mL−1). Indices selected for this study were:
n-C17/Pristane (nC17/Pr),
n-C18/Phytane (nC18/Ph) in order to
evaluate the relative biodegradation of n-alkanes.
derivates (TERHCs) were analysed by high-resolution GC-FID (DANI Master
GC Fast Gas Chromatograph System, DANI Instruments Sp.A., Milan).
After acidification, TERHCs from samples were extracted at room temperature on a
shaking table by using dichloromethane (CH2Cl2,
Sigma-Aldrich, Milan; 10% v/v). This procedure was repeated three times, and the
CH2Cl2 phase was combined and treated with sodium
sulfate anhydrous (Na2SO4, Sigma-Aldrich, Milan) in order
to remove any residual water (
et al., 1991
et al., 2005
rotary evaporation (Rotavapor model R110; Büchi Labortechnik AG, Switzerland) at
room temperature (< 30 °C), followed by evaporation under a stream of
nitrogen and taken up into a solution containing heptamethyl-nonane as an
internal standard (79 μg mL−1). Indices selected for this study were:
n-C17/Pristane (nC17/Pr),
n-C18/Phytane (nC18/Ph) in order to
evaluate the relative biodegradation of n-alkanes.
6
Functionalization of Silicon Surfaces
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N-type phosphorus-doped silicon (111) wafers,
with resistivity of 0.01–0.018 Ω·cm, were used in
these experiments. Heptadecafluoro-1,1,2,2-tetrahydrodecyl) dimethylchlorosilane
(95% purum), (heptadecafluoro-1,1,2,2-tetrahydrodecyl)methyldichlorosilane
(97% purum) and 1H,1H,2H,2H-perfluorodecyltrichlorosilane (97% purum, stabilized
with copper) were purchased from abcr GmbH. Chloro-decyl-dimethylsilane,
acetone, diethyl ether, CH2Cl2 and triethylamine
(Et3N) were purchased from Sigma-Aldrich. For surface modification,
CH2Cl2 was dried in a PureSolv EN solvent purification
system (Innovative Technology). Deionized (DI) water was obtained
from a Milli-Q Integral water purification system (Merck-Millipore).
Phosphate buffered saline (PBS, 10 mM, pH 7.4) was prepared from a
solution of NaCl (8.01 g/L), Na2HPO4 (1.41 g/L),
KH2PO4 (0.27 g/L) and KCl (0.20 g/L) in DI water.
with resistivity of 0.01–0.018 Ω·cm, were used in
these experiments. Heptadecafluoro-1,1,2,2-tetrahydrodecyl) dimethylchlorosilane
(95% purum), (heptadecafluoro-1,1,2,2-tetrahydrodecyl)methyldichlorosilane
(97% purum) and 1H,1H,2H,2H-perfluorodecyltrichlorosilane (97% purum, stabilized
with copper) were purchased from abcr GmbH. Chloro-decyl-dimethylsilane,
acetone, diethyl ether, CH2Cl2 and triethylamine
(Et3N) were purchased from Sigma-Aldrich. For surface modification,
CH2Cl2 was dried in a PureSolv EN solvent purification
system (Innovative Technology). Deionized (DI) water was obtained
from a Milli-Q Integral water purification system (Merck-Millipore).
Phosphate buffered saline (PBS, 10 mM, pH 7.4) was prepared from a
solution of NaCl (8.01 g/L), Na2HPO4 (1.41 g/L),
KH2PO4 (0.27 g/L) and KCl (0.20 g/L) in DI water.
7
Synthesis of Moisture-Sensitive Organic Compounds
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All moisture-sensitive
reactions were conducted in oven-dried glassware under an atmosphere
of dry nitrogen. Reaction solvents (CH2Cl2,
Et2O, THF, DMF) were purchased from Sigma-Aldrich in anhydrous
form. All other solvents and reagents were purchased from commercial
suppliers and used as received unless otherwise specified. Thin-layer
chromatography (TLC) was performed with glass plates precoated with
silica 60 Å F254 (250 mm) and visualized by UV light. 1H and 13C NMR spectra were recorded using a 500 MHz Bruker
instrument working at a frequency of 500 MHz for 1H and
at 126 MHz for 13C. Chemical shifts are reported in ppm
using residual solvent resonances as internal reference (d 7.26 and
d 77.0 for 1H and 13C in CDCl3, DMSO-d6 2.50 and DMSO-d6 39.51 for 1H and 13C in DMSO-d6). 1H NMR data are reported as follows: b
= broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.
Coupling constants are given in hertz. The purity of all compounds
and synthetic intermediates was judged to be 95% or better based on 1H NMR. IR measurements were performed in a Nicolet FTIR as
thin films. High-resolution mass spectrometry analyses were conducted
at the Purdue University Bentley and/or Chemistry Mass Spectrometry
facility.
reactions were conducted in oven-dried glassware under an atmosphere
of dry nitrogen. Reaction solvents (CH2Cl2,
Et2O, THF, DMF) were purchased from Sigma-Aldrich in anhydrous
form. All other solvents and reagents were purchased from commercial
suppliers and used as received unless otherwise specified. Thin-layer
chromatography (TLC) was performed with glass plates precoated with
silica 60 Å F254 (250 mm) and visualized by UV light. 1H and 13C NMR spectra were recorded using a 500 MHz Bruker
instrument working at a frequency of 500 MHz for 1H and
at 126 MHz for 13C. Chemical shifts are reported in ppm
using residual solvent resonances as internal reference (d 7.26 and
d 77.0 for 1H and 13C in CDCl3, DMSO-d6 2.50 and DMSO-d6 39.51 for 1H and 13C in DMSO-d6). 1H NMR data are reported as follows: b
= broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.
Coupling constants are given in hertz. The purity of all compounds
and synthetic intermediates was judged to be 95% or better based on 1H NMR. IR measurements were performed in a Nicolet FTIR as
thin films. High-resolution mass spectrometry analyses were conducted
at the Purdue University Bentley and/or Chemistry Mass Spectrometry
facility.
8
Optimized Organic Synthesis Techniques
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Chemicals were purchased from Sigma-Aldrich
or Fluorochem and were used without purification. Solvents were purchased
from VWR Chemicals (CH2Cl2) or Sigma-Aldrich
[toluene, dioxane, and dimethyl sulfoxide (DMSO)] and used without
purification unless stated otherwise. Dry solvents were dried over
an inert PS-MD-5 solvent purification system, equipped with an activated
alumina/copper wire column. Microwave reactions were performed in
a closed vessel in a Biotage Initiator, measuring temperature by IR. 1H NMR measurements were acquired on a Bruker AVANCE 300 (300.13
MHz) or Bruker AVANCE 500 (500.23 MHz) spectrometer. 13C NMR measurements were acquired on a Bruker AVANCE 500 (125.78 MHz)
spectrometer. Chemical shifts are reported in parts per million downfield
of tetramethylsilane and are corrected according to the solvent. Mass
analysis was performed using a Bruker MicrOTOF-Q instrument on a positive
ion polarity mode for ESI (electrospray ionization). Capillary charge:
4000 V. Melting points were measured using a Büchi M-565 melting
point apparatus. SiO2 column chromatography was performed
using Merck silica gel C60 (particle size 40–60 μm).
Thin-layer chromatography (TLC) was performed on Merck silica gel
C60 F254 plates (silica coat on the aluminum support). All isolated
yields are corrected for impurities (if present).
or Fluorochem and were used without purification. Solvents were purchased
from VWR Chemicals (CH2Cl2) or Sigma-Aldrich
[toluene, dioxane, and dimethyl sulfoxide (DMSO)] and used without
purification unless stated otherwise. Dry solvents were dried over
an inert PS-MD-5 solvent purification system, equipped with an activated
alumina/copper wire column. Microwave reactions were performed in
a closed vessel in a Biotage Initiator, measuring temperature by IR. 1H NMR measurements were acquired on a Bruker AVANCE 300 (300.13
MHz) or Bruker AVANCE 500 (500.23 MHz) spectrometer. 13C NMR measurements were acquired on a Bruker AVANCE 500 (125.78 MHz)
spectrometer. Chemical shifts are reported in parts per million downfield
of tetramethylsilane and are corrected according to the solvent. Mass
analysis was performed using a Bruker MicrOTOF-Q instrument on a positive
ion polarity mode for ESI (electrospray ionization). Capillary charge:
4000 V. Melting points were measured using a Büchi M-565 melting
point apparatus. SiO2 column chromatography was performed
using Merck silica gel C60 (particle size 40–60 μm).
Thin-layer chromatography (TLC) was performed on Merck silica gel
C60 F254 plates (silica coat on the aluminum support). All isolated
yields are corrected for impurities (if present).
9
Spectroscopic Characterization of Novel Compounds
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UV spectra were measured on a Milton Roy Spectronic 300 Array spectrophotometer, and the IR was recorded on a Perkin-Elmer FT-IR 1760x spectrophotometer (Boston, MA, USA). High-resolution electrospray ionization mass spectra (HR-ESI-MS) were recorded with a Bruker micro TOF mass spectrometer (Billerica, MA, USA). NMR spectra were obtained with a Bruker Avance DPX-300 or Avance III HD 500FT-NMR spectrometer (Billerica, MA, USA). MeOH, EtOAc, n-butanol, hexane, CH2Cl2, yeast α-glucosidase, p-NPG, glucose oxidase (GO) assay kit, sodium dodecyl sulfate (SDS), 3-(4,5- dimethyl thiazol-2-yl)-5-diphenyl tetrazolium bromide (MTT), and acarbose were obtained from Sigma-Aldrich (St. Louis, MO, USA). Alpha minimal essentialmedium (α-MEM), fetal bovine serum (FBS), and penicillin-streptomycin (10,000 IU/mL) were purchased from Thermo Fisher Scientific (Grand Island, NY, USA). Insulin (100 IU/mL) was acquired from Biocon (Bangalore, India). Silica gel (SiO2) and TLC plates were obtained from Merck (Darmstadt, Germany), and Sephadex LH-20 was from Pharmacia (Piscataway, NJ, USA).
10
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.
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