Silver oxide, anhydrous sodium sulfate, iodomethane, iodomethane-d3, l -phenylalanine methyl ester hydrochloride, mass spectrometric grade formic acid (~98%), and HPLC grade trifluoroacetic acid (99.0%) were obtained from Sigma-Aldrich; HPLC grade methanol, acetonitrile, ethyl acetate, and water from Fisher Scientific; Deuterium oxide (99.8%) and HPLC grade dichloromethane from Acros; l -alanyl-l -proline, N-(tert-butoxycarbonyl)-d -alanine, l -proline tert-butyl ester hydrochloride, d -proline tert-butyl ester hydrochloride, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) hydrochloride from Tokyo Chemical Industry. A Fisher Scientific vortex mixer was used for mixing and a Sorvall Legend Micro 21R microcentrifuge used for centrifugation of 1.5 mL Eppendorf tubes. A Corning Laboratory stirrer was used for mixing chemical reactions. Human plasma (Na2-EDTA) was obtained from Bioreclamation and stored at −80 °C. An Argonaut SPE DRY™ 96 DUAL evaporator was used for solvent evaporation.
Silver oxide
Manufactured by Merck Group
Sourced in Germany, Canada
Silver oxide is a chemical compound with the formula Ag2O. It is a gray-black solid that is used as a component in various types of laboratory equipment and instruments.
Automatically generated - may contain errors
Lab products found in correlation
Benzyl bromide, by Merck Group (2 mentions)
Ethyl iodide, by Merck Group (2 mentions)
4 5 diphenylimizadole, by Thermo Fisher Scientific (2 mentions)
Lithium bis trimethyl silyl amide, by Thermo Fisher Scientific (2 mentions)
Deuterated solvent, by Cambridge Isotopes (2 mentions)
Haucl4, by Strem Chemicals (2 mentions)
Deuterium oxide, by Thermo Fisher Scientific (1 mentions)
Trifluoroacetic acid hplc grade, by Merck Group (1 mentions)
Iodomethane d3, by Merck Group (1 mentions)
L phenylalanine methyl ester hydrochloride, by Merck Group (1 mentions)
Hplc grade dichloromethane, by Thermo Fisher Scientific (1 mentions)
Hplc grade methanol, by Thermo Fisher Scientific (1 mentions)
Iodomethane, by Merck Group (1 mentions)
Anhydrous sodium sulfate, by Merck Group (1 mentions)
Ammonium hydroxide, by Merck Group (1 mentions)
Sodium borohydride, by Merck Group (1 mentions)
Epibromohydrin, by Merck Group (1 mentions)
Dichloromethane dcm, by Merck Group (1 mentions)
Hydrochloric acid (hcl), by Merck Group (1 mentions)
Nitric acid, by Merck Group (1 mentions)
7 protocols using silver oxide
1
Synthesis and Analysis of Labeled Metabolites
2
Synthesis of Gold Compound Au-1
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The preparation of gold compound Au-1 was was performed following a reported synthetic method. 53 (link) H[AuCl 4 ] was purchased from Strem Chemicals (Newburyport, MA). Benzyl bromide, ethyl iodide, and silver oxide were purchased from Sigma Aldrich (St. Louis, MO). 4,5-diphenylimizadole and lithium bis(trimethyl silyl)amide were purchased from Alfa Aesar (Haverhill, MA). Reaction solvents were purchased anhydrous from Fisher Scientific (BDH, ACS Grade) and Sigma-Aldrich. Solvents were dried in a SPS machine, and kept over molecular sieves (3 Å, beads, 4-8 mesh); otherwise over sodium, if necessary. Deuterated solvents were purchased from Cambridge Isotope Laboratories, Inc., and were kept over molecular sieves (3 Å, beads, 4-8mesh). Celite (Celite 545, Diatomaceous Earth) was purchased from VWR International and used as received.
3
Extraction of Taxus wallichiana Compounds
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Silver oxide, ammonium hydroxide and sodium borohydride were acquired from Sigma Aldrich (Germany). Taxus wallichiana leaves used in this experiment were collected from the northern areas of Pakistan, which include Nathia Gali and Donga Gali.
4
Synthesis of Oligo(PFPAE) Derivatives
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Oligo(PFPAE) diacyl fluoride was synthesized via the anionic ring-opening polymerization of hexafluoropropoxide (HFPO, generously supplied by Chemours™, USA), following the procedure described elsewhere [39 –42 (link)]. Different batches of the synthesized oligo(PFPAE) diacyl fluoride were mixed to be used for the syntheses of vinyl ether derivatives. Oligo(PFPAE) dicarboxylic acid, obtained by hydrolysis of the acyl fluoride, was used for the synthesis of the epoxy derivatives.
The chemicals employed for the functionalization of the oligo(PFPAE) are the following: 1,1,1,3,3-pentafluorobutane (PFB) was purchased from Alfa Aesar (Ward Hill, Massachusetts, USA). Epibromohydrin, ethylene glycol vinyl ether (EGVE), 1,4-Butylene glycol divinyl ether (BGVE), di(ethylene glycol) vinyl ether (DEGVE), silver oxide, 4-dimethylaminopyridine (DMAP), diethyl ether (Et2O), ethyl acetate (EtOAc), Triethylamine (Et3N), acetonitrile (MeCN), and dichloromethane (DCM), and all other chemicals were purchased from Sigma Aldrich (Canada). PFB, Et3N, MeCN, and DCM were dried for 48 h over preconditioned 3 Å molecular sieves (20% w v−1).
The chemicals employed for the functionalization of the oligo(PFPAE) are the following: 1,1,1,3,3-pentafluorobutane (PFB) was purchased from Alfa Aesar (Ward Hill, Massachusetts, USA). Epibromohydrin, ethylene glycol vinyl ether (EGVE), 1,4-Butylene glycol divinyl ether (BGVE), di(ethylene glycol) vinyl ether (DEGVE), silver oxide, 4-dimethylaminopyridine (DMAP), diethyl ether (Et2O), ethyl acetate (EtOAc), Triethylamine (Et3N), acetonitrile (MeCN), and dichloromethane (DCM), and all other chemicals were purchased from Sigma Aldrich (Canada). PFB, Et3N, MeCN, and DCM were dried for 48 h over preconditioned 3 Å molecular sieves (20% w v−1).
5
Synthesis of Gold Compounds
6
Cerium-Based Chemical Extraction Protocol
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Experiments were conducted using the following chemical
reagents:
cerium ammonium nitrate ((NH4)2Ce(NO3)6, denoted as CAN, Aldrich, ≥98.5%), tributylphosphate
(denoted as TPB, Aldrich, ≥99%), hydrogenated tetrapolypropylene
(mixture of branched alkanes of the general formula, C12H26, denoted as HTP, from the ORANO La Hague plant, France,
CAS Number 68551-17-7), nitric acid (HNO3, Aldrich, 65%),
and deionized water. Other reactants were purchased from Aldrich for
the quantitative chemical analysis of Ce4+/Ce3+ solutions: silver oxide (AgxO), Arsenazo-III,
sodium oxalate (≥99.5%), glycine (≥99%),l -ascorbic
acid, and hydrochloric acid (HCl, 37%). All chemical reagents (except
HTP) are commercially available and were used without any further
purification.
reagents:
cerium ammonium nitrate ((NH4)2Ce(NO3)6, denoted as CAN, Aldrich, ≥98.5%), tributylphosphate
(denoted as TPB, Aldrich, ≥99%), hydrogenated tetrapolypropylene
(mixture of branched alkanes of the general formula, C12H26, denoted as HTP, from the ORANO La Hague plant, France,
CAS Number 68551-17-7), nitric acid (HNO3, Aldrich, 65%),
and deionized water. Other reactants were purchased from Aldrich for
the quantitative chemical analysis of Ce4+/Ce3+ solutions: silver oxide (AgxO), Arsenazo-III,
sodium oxalate (≥99.5%), glycine (≥99%),
acid, and hydrochloric acid (HCl, 37%). All chemical reagents (except
HTP) are commercially available and were used without any further
purification.
7
Synthesis of N-Alkylated Pyridine Derivatives
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All manipulations were performed under nitrogen atmosphere unless stated otherwise. All anhydrous solvents, n-butyllithium (n-BuLi; 2.5 M solution in hexane), paraformaldehyde (PFA), 1-chloro-4-iodobutane (Cl(CH2)4I), HCl (37%), sodium azide (NaN3), sodium iodide (NaI), potassium iodide (KI), triphenylphosphine (PPh3), sodium sulfate (Na2SO4), magnesium sulfate (MgSO4), sodium thiosulfate (Na2S2O3), trans-3-(3′-pyridyl)acrylic acid (C5NH4(CH)2COOH), thionyl chloride (SOCl2), Hünig’s base or N,N-diisopropylethylamine (DIPEA), pyridine (C5H5N), chloromethyl chloroformate (ClCH2CO2Cl), diethylene glycol, tosyl chloride (TsCl), silver oxide (Ag2O), propargyl bromide (CHCCH2Br), chromium trioxide (CrO3), and dansyl chloride were purchased from Aldrich and used as received. All solvents were dried using 3 Å molecular sieves (20%, m/v).33 (link) Silica gel was purchased from Sorbent Technologies (60 Å, 63–200 μm).
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