2 chloro 1 methylpyridinium iodide

HPLC grade MeOH, acetonitrile (ACN), dimethylformamide (DMF, Pharmaceutical Secondary Standard grade), 2,6-di-tert-butyl-4-methylphenol, triethylamine, DMED, and 2-chloro-1-methylpyridinium iodide were purchased from Sigma-Aldrich Co. LLC (St. Louis, MO). RvD1, RvD2, and RvD4; LxA4 and LxB4; maresin 1 and Mar2; 9,10-DiHOME, 12,13-DiHOME, 5S, 6R-Lipoxin A4-19,19,20,20,20-d5; and Resolvin D1-21,21,22,22,22-d5 were supplied by Cayman Chemical Co. (Ann Arbor, MI). 18S-Resolvin E3 and 18R-Resolvin E3 (RvE3R) were prepared as described previously (15 , 16 (link)). HPLC grade formic acid (FA) was obtained from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Ultrapure water was prepared using a puric ω (Organo, Co., Tokyo, Japan). The HF Bond Elut C18 (1 ml, 50 mg) was purchased from Agilent Technologies, Inc. (Santa Clara, CA).

N-isopropylacrylamide (Sigma Aldrich, 99%), Triethylamine (BDH, HPLC Grade, 99.5%), Dimethylforamide (DMF) (BDH, spectroscopy Grade, 99.5%), 4,4′-azobis(4-cyanovaleric acid), (Sigma Aldrich, ≥ 75%) as initiator, 4-hydroxy-TEMPO (Sigma Aldrich, 97%) as terminator, 2-chloro-1-methylpyridinium iodide (Sigma Aldrich, 97%) as coupling agent for cyclization, Methanol (Merck, Chromatography Grade, 99.8%), deionized water and CO₂ gas (99.99%, Fadak company of Iran) were purchased and applied for this research.

Simvastatin, ethylenediamine, methyl acrylate, succinic anhydride, α-D-glucoheptono-1,4-lactone (GHL), carbonyl diimidazole (CDI), 2-chloro-1-methylpyridinium iodide, 4-dimethylaminopyridine (DMAP), triethylamine (TEA), R-glycidol, dimethyl sulfoxide (DMSO), and other reagents used in syntheses were obtained from Merck KGaA (Darmstadt, Germany). Celecoxib was purchased from Abcam GmbH (Karlsruhe, Germany), while biotin N-hydroxysuccinimide ester (NHS-Biotin) was obtained from AmBeed (Arlington Hts, IL, USA). Spectra/Por^® 3 RC dialysis membrane (cellulose, MW_cutoff—3.5 kD) was provided by Carl Roth GmbH and Co. KG (Karlsruhe, Germany).