Deuterated chloroform cdcl3

Silica gel column chromatography was performed with Silica gel 60 (20–230 mesh; Nacalai Tesque Inc., Kyoto, Japan) or Wakogel C-300 HG (Fujifilm Wako Pure Chemical Corporation, Osaka, Japan). Precoated TLC was performed on Silica gel 60 F₂₅₄ plates (Fujifilm Wako Pure Chemical Corporation). NMR spectra were recorded using a JNM-ECS400 NMR spectrometer (JEOL Ltd., Akishima, Tokyo, Japan), which was operated at 400 MHz (¹H) and 100 MHz (¹³C). Tetramethylsilane (internal standard of NMR spectrometry), deuterated chloroform (CDCl₃), and deuterated methanol (CD₃OD) were obtained from Euriso-Top (Saint-Aubin, France). Optical rotations of compounds were measured on a DIP-1000 polarimeter (JASCO Corporation, Hachioji, Tokyo, Japan). EI–MS spectra were obtained with a JMS-700 MStation mass spectrometer (JEOL Ltd.). ChemDraw software (PerkinElmer Inc., Waltham, MA, USA) was used to draw chemical structures.

For the biological test, bacto tryptone and bacto yeast extract were provided by Fisher Scientific (Illkirch, France). Potassium phosphate monobasic, potassium phosphate dibasic, and agar were purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France).
For extraction, purification, and chemical analysis, chloroform, ethyl acetate, methanol, formic acid, and water (of ULC-MS grade) were all purchased from Biosolve BV (Valkenswaard, The Netherlands). Hydrochloric acid solution (1M) was purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France). Deuterated reagent, such as deuterated chloroform (CDCl₃), was purchased from Euriso-top (Saint-Aubin, France).
For organic synthesis, tropolone, 18-crown-6, iodomethane, N-bromosuccinimide, trifluoroacetic acid, and acetic anhydride were purchased form Thermo Scientific (Illkirch, France). Benzene and toluene were purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France).

Styrene (S) (≥99%), sodium azide (NaN₃) (≥99%), N,N-dimethylformamide (DMF)
(≥99.9%), cyanomethyl dodecyl carbonotrithioate (CMDTC) (98%), n-hexane (Hex) (≥97%), carbon disulfide (CS₂) (≥99.9%), and trifluoroacetic acid (TFA) (≥98%) were
purchased from Merk (Sigma-Aldrich). 1,3-Bis(diphenylphosphino)propane
(DPPP) (>98%) and 1,4-bis(diphenylphosphino)butane (DPPB) (>98%)
were
supplied by TCI. Tetrahydrofuran (THF) (GPC grade) was purchased from
Scharlau. 2,2′-Azobis(2-methylpropionitrile) (AIBN) (≥97%)
was purchased from Fisher Scientific. 2,3,4,5,6-PentafluoroStyrene
(PFS) (98%) and trimethylsilanol (Me₃SiOH) (96.85%) were
purchased from BLDpharm. Deuterated chloroform (CDCl₃)
(99.50% D, 0.03% TMS v/v) and deuterated tetrahydrofuran (THF-d₈) (99.50% D, water <0.05%) were purchased from Eurisotop.
Unless otherwise specified, all reagents were used as received without
further purification. To remove the inhibitor, S and PFS were purified
by passing through a column packed with activated basic alumina.

All reagents were commercially available materials and were used without further purification. (+)-(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid (≥98%) was provided from AmBeed (Arlington Heights, IL, USA). L-proline (≥98.5%) was obtained from Carl Roth (Karlsruhe, Germany). Trimethylsilyl chloride (≥99%) (TMSCl) was purchased from Sigma-Aldrich (Steinheim am Albuch, Germany). Ammonium hydroxide solution 25% (NH₃∙H₂O) was of analytical grade obtained from StanLab (Lublin, Poland). Methanol (MeOH), ethanol (EtOH), propan-2-ol (i-PrOH), propan-1-ol (PrOH), butan-1-ol (BuOH), dimethyl sulfoxide, chloroform, ethyl acetate, diethyl ether, toluene, and n-hexane of high purity were purchased from Chempur (Gliwice, Poland). Deuterated chloroform (CDCl₃) (99.8%) (+0.03% TMSCl) was provided by Eurisotop (Cheshire, England). Acetonitrile was provided by J.T. Baker (Radnor, Pennsylvania, USA). PBS (pH 7.4), potassium dihydrogen phosphate (p.a.) was purchased from Merck (Darmstadt, Germany). For cell culture studies, murine fibroblast cell line, L929, and all cell culture reagents were purchased from Sigma Aldrich (Poznań, Poland), while all sterile, single-use cell culture plasticware was purchased from VWR (Gdańsk, Poland).

Rosiglitazone (RSG), sodium cholate hydrate, poly(vinyl alcohol) (PVA), phosphate buffered saline (PBS), cell culture reagent MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide), and Lipopolysaccharides (LPS) were purchased from Sigma-Aldrich (Saint-Quentin-Fallavier, France). Radioactive Rosiglitazone [benzylidene-3H] was obtained from ARC (Washington, DC, USA). DL-lactide was purchased from Biovalley, Polysciences Inc. (Warrington, PA, USA). Poly(ethylene glycol) methyl ether (OH-PEG-OCH₃, average M_n = 5000 g/mol), stannous 2-ethyl hexanoate (stannous octoate, Sn(Oct)₂), dried toluene, poly(vinyl alcohol) (PVA) (M_w = 30,000–70,000 g/mol, 87–90% hydrolyzed), D₂O were provided by Sigma-Aldrich (Saint-Quentin-Fallavier, France). Deuterated chloroform (CDCl₃) and deuterated acetone (acetone-d) were obtained from Euriso-top (Saint-Aubin, Essonne, France). All solvents were purchased from Carlo Erba (Val-de-Reuil, France). Water was purified using a RIOS/Synergy system from Millipore (Molsheim, France). NMR sample tubes and coaxial inserts were obtained from CortecNet (Bretonneux, France).

3,5-Bis(2-dodecylthiocarbonothioylthio-1-oxopropoxy)benzoic acid (BTCBA, 98%), 2-(Dodecylthiocarbonothioylthio)propionic acid (DTPA, 98%), acryloyl chloride (≥97%), triethylamine (TEA, ≥99%), 2-methyltetrahydrofuran (Me-THF, 99.5%), n-Butyl acrylate (BA, 99%), butyl l-lactate (98%) were all purchased from Merck KGaA (Darmstadt, Germany) and used as received unless otherwise specified. Thus, BA was passed through a short column of basic Al₂O₃ prior to use in order to remove the radical inhibitor and both TEA and Me-THF were distilled prior to use from CaH₂ and sodium/benzophenone, respectively. 2,2′-Azobis(2-methylpropionitrile) [AIBN, ≥98%, Fluka (Buchs, Switzerland)] was recrystallized three times from methanol before further use. Deuterated chloroform (CDCl₃) was purchased from Eurisotop, and ethyl-5-(dimethylamido)-2-methyl-5-oxopentanoate (Rhodiasolv^® PolarClean) was kindly donated by Solvay (Aubervilliers, France). Isosorbide acetate, i.e., isosorbide 2-acrylate-5-acetate and vanillin acrylate monomers were prepared following previously reported synthetic procedures [32 (link),33 (link),34 (link)].