C10, C12, C14, and C16 epoxides were purchased from TCI or Sigma. C15 epoxide was not commercially available and was synthesized by the dropwise addition of 1-pentadecene (TCI) to a 2× molar excess of 3-chloroperbenzoic acid (Sigma) in dichloromethane (BDH) under constant stirring at room temperature. After reacting for 8 h, the reaction mixture was washed with equal volumes of super saturated aqueous sodium thiosulfate solution (Sigma) three times. After each wash, the organic layer was collected using a separation funnel. Similarly, the organic layer was then washed three times with 1 M NaOH (Sigma). Anhydrous sodium sulfate was added to the organic phase and stirred overnight to remove any remaining water. The organic layer was concentrated under vacuum to produce a slightly yellow, transparent oily liquid. This liquid was vacuum distilled to produce the clear, colorless C15 epoxide liquid.
3 chloroperbenzoic acid
Manufactured by Merck Group
Sourced in Germany
3-chloroperbenzoic acid is a chemical compound used as an oxidizing agent in various laboratory applications. It is a white crystalline solid with the molecular formula C₇H₅ClO₃. The compound serves as a source of peroxycarboxylic acid, which is useful for a range of synthetic and analytical procedures.
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Lab products found in correlation
1 m naoh, by Merck Group (1 mentions)
Sodium sulfite, by Merck Group (1 mentions)
Allyl bromide, by Merck Group (1 mentions)
Ethyl ether anhydrous, by Thermo Fisher Scientific (1 mentions)
Anhydrous magnesium sulfate, by Thermo Fisher Scientific (1 mentions)
Sodium chloride (nacl), by Thermo Fisher Scientific (1 mentions)
Ethyl acetate, by Thermo Fisher Scientific (1 mentions)
Hexane, by Thermo Fisher Scientific (1 mentions)
Acetonitrile, by Thermo Fisher Scientific (1 mentions)
Sodium bicarbonate, by Thermo Fisher Scientific (1 mentions)
Methanol, by Thermo Fisher Scientific (1 mentions)
Hydroquinone, by Merck Group (1 mentions)
Chloroform, by Thermo Fisher Scientific (1 mentions)
1 6 dibromohexane, by Merck Group (1 mentions)
Sodium hydrosulfite, by Merck Group (1 mentions)
Thionyl chloride, by Merck Group (1 mentions)
1 4 dibromobutane, by Merck Group (1 mentions)
1 3 dibromopropane, by Merck Group (1 mentions)
1 5 dibromopentane, by Merck Group (1 mentions)
4 hydroxybezoic acid, by Merck Group (1 mentions)
5 protocols using 3 chloroperbenzoic acid
1
Synthesis and Purification of C15 Epoxide
2
Synthesis of Halogenated Monomers
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1,2-Dibromeoethane (99%), 1,3-dibromopropane (99%), 1,4-dibromobutane (99%), 1,5-dibromopentane (97%), 1,6-dibromohexane (98%), 1,7-dibromopentane (97%), 1,8-dibromooctane (98%), hydroquinone (99%), sodium hydrosulfite (technical grade), sodium sulfite (98%), 3-chloroperbenzoic acid (≤77%), thionyl chloride (99%), allyl bromide (99%), 4-hydroxybezoic acid (99%), and pyridine (anhydrous, 99.8%) were purchased from Sigma Aldrich and used without further purification. Sodium bicarbonate (99%), magnesium sulfate anhydrous (99%), sodium chloride (99%), hexanes (98.5%), ethyl acetate (99.5%) and ethyl ether anhydrous (99%), and methanol (ACS grade) were purchased from Fisher Chemical and used without further purification. Chloroform (HPLC grade), methylene chloride (HPLC), and acetonitrile (anhydrous), was purchased from Fisher Chemical and stored with activated molecular sieves to remove water. Sodium sulfate anhydrous (99%) and potassium hydroxide (85%) were purchased from Oakwood Chemical and used without further purification. Hydrochloric acid (10M) was purchased from Ricca Chemical and used without further purification. Sulfuric acid (95%) was purchases from VWR analytical and used without further purification. Ethanol anhydrous (99.9%) was purchased from Decon and used without further purification. Synthesis details of Cx diepoxy monomer is shown in SI Appendix .
3
Quantitative Analysis of Deterenol Acetate
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Iodomethane (purum), potassium carbonate (p.a.), IPNS (Deterenol acetate), 3‐chloroperbenzoic acid (<77%), acetone, lithium aluminium hydride (powder, 95%), potassium carbonate (>99%), sulfur trioxide pyridine complex (97%), and octopamine hydrochloride (analytical standard) were obtained from Sigma‐Aldrich (Deisendorf, Germany), acetonitrile, formic acid, and ammonium acetate (all analytical grade) were purchased from Merck (Darmstadt, Germany), and solid‐phase extraction cartridges (OASIS HLB, 3 mL, 60 mg sorbent) were obtained from Waters (Eschborn, Germany). The internal standard IPNS‐d7 (deterenol‐d7) was provided by LGC Standards GmbH (Wesel, Germany).
4
Biocatalytic Oxidation Reaction Protocols
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3,3,5‐trimethylcyclohexanone (98%, Sigma‐Aldrich), sodium phosphite dibasic pentahydrate (> 98%, Sigma Aldrich), dichloromethane (Biosolve), hexadecane (99.5%, TCI), acetonitrile (Biosolve), 1,4‐dioxane (Sigma Aldrich), methanol (Biosolve), ethanol (Biosolve), 1,3‐dioxolane (Acros organics), and ethyl acetate (Biosolve) were used as received. 3‐Chloroperbenzoic acid (70%, Sigma Aldrich) was stored at –4 °C. β‐Nicotinamide adenine dinucleotide phosphate reduced tetrasodium salt NADPH (95%, Alfa Aesar) and β‐nicotinamide adenine dinucleotide phosphate disodium salt NADP+ (97%, Alfa Aesar) were stored at –20 °C and solutions, in buffer, were prepared fresh prior to use.
5
Synthesis and Characterization of Fluorescent Polymer Nanoparticles
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All the materials were used without any further purification. 2,2,6,6-Tetramethyl-4-piperidyl methacrylate (>98%; PMA) was purchased from TCI Chemicals Pvt. Ltd. Glycidyl methacrylate (≥98%; GMA) and poly(ethyleneglycol)methylether 4-cyano 4[(dodecylsulfanylthiocarbonyl)sulfanyl] pentanoate (PEGmacro-CTA; Mn = 10 kDa) were purchased from Sigma. We measured Mp = 8300 g mol−1 by SEC see Fig. 2 and Mn = 9.8 kg mol−1 by NMR. 6-Aminofluorescein (≥95%; 6-AF), 3-chloroperbenzoic acid (≥78%; mCPBA) and 2,2′-azobis(2-methylpropionitrile) (≥98%; AIBN) were purchased from Sigma. Human LDL (Sigma-Aldrich) and Oil Red O solution (0.5% in isopropanol, Sigma-Aldrich) were purchased from Sigma. Hoechst 33342 Solution (20 mM) (Thermo Scientific™), ProLong® Gold mount media (Thermo Fisher Scientific), Nunc™ MicroWell™ 96-Well Microplates – Thermo Fisher Scientific, Total Antioxidant Capacity Assay Kit (Sigma-Aldrich), Cell Counting Kit – 8 (Sigma-Aldrich), Dulbecco's Phosphate Buffered Saline (PBS) (Cell culture grade, Sigma-Aldrich), DMEM (Dulbecco's Modified Eagle's medium) (Sigma-Aldrich), chloroform-d 99.8 atom % D (≥99.8%, Sigma-Aldrich), dichloromethane ≥99.8% stabilized.
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