Oxalyl chloride

A poly(ethylene terephthalate) (PET) substrate-laminated PEDOT:PSS (200 nm thick) thin film (Orgacon® F350, Agfa-Gebhardt, Tokyo, Japan) was used. Oxalyl chloride was purchased from Tokyo Chemical Industry (Tokyo, Japan). 6-Carboxypyridine-3-boronic acid, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), and SA were purchased from Fujifilm Wako Pure Chemicals (Tokyo, Japan). Fetal bovine serum (FBS) was purchased from Funakoshi (Tokyo, Japan). All other reagents were of extra-pure grade, obtained from commercial sources, and used as received. Milli-Q water (18.2 MΩ cm, Merck, Darmstadt, Germany) was used in all experiments.

Phosphatidylcholine (PC) D₃₁-16:0/18:1, phosphatidylethanolamine (PE) D₃₁-16:0/18:1, and SM d18:1/D₃₁-16:0 were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). All chemicals used in the mobile phases were purchased from Fujifilm Wako Pure Chemical Corporation (Osaka, Japan). Deuterium-labeled (12,12,13,13-D₄) hexacosanoic acid (FA D₄-26:0) and deuterium-labeled (9,10-D₂) oleic acid (FA D₂-18:1) were purchased from Cambridge Isotope Laboratories, Inc. (Andover, MA). Methyl-β-cyclodextrin (MβCD) was obtained from Sigma-Aldrich, Inc. (St. Louis, MO). FA D₄-26:0 and FA D₂-18:1 were dissolved in CHCl₃/methanol (1:1 by volume, 3 mM each), and MβCD was dissolved in water (50 mM) and stored at −20°C. Deuterium-labeled palmitic acid (FA D₃₁-16:0) and CoA were purchased from Santa Cruz Biotechnology (Dallas, TX) and the Oriental Yeast Co., Ltd. (Kyoto, Japan), respectively. Oxalyl chloride was purchased from Tokyo Chemical Industry (Tokyo, Japan). Other organic solvents used in the synthesis of FA D₃₁-16:0 were purchased from Fujifilm Wako Pure Chemical Corporation.

α-Methoxy-ω-amino poly(ethylene glycol) (MeO-PEG-NH₂) (M_w = 12,000 g mol⁻¹) was purchased from NOF CORPORATION (Tokyo, Japan). ξ-Trifluoroacetyl-l-lysine N-carboxyanhydride (Lys-(TFA)-NCA) was purchased from Chuo Kaseihin Co. Inc. (Tokyo, Japan). N,N-dimethylformamide (DMF) (purity > 99.5%) and methanol (purity > 99.5%) were purchased from Fujifilm Wako Pure Chemical, Co., Inc., (Tokyo, Japan). Diethyl ether (purity > 95%), cis-aconitic anhydride (CAA; purity > 95%), dextran sulfate (M_r ~40,000), and 4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) (1.0 M), Dulbecco’s phosphate-buffered saline (D-PBS), fetal bovine serum (FBS), penicillin-streptomycin and RPMI-1640 medium were purchased from Sigma-Aldrich (St. Louis, MO, USA). Oxalyl Chloride (purity > 98%) and anhydrous dichloromethane (purity > 98%) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). The CT26 cells were obtained from Riken BioResource Center (Tsukuba, Japan).