Sodium methoxide

Poly(ethylene glycol)s with a number-average molecular weight of 600 g/mol was purchased from Wako Pure Chemical Industries, Ltd. (current FUJIFILM Wako Pure Chemical Co., Osaka, Japan). It was dried before use by a two-stage process: an azeotropic distillation with toluene and a subsequent 4 h heating at 120 °C under a dynamic vacuum. Ethyl lactate was purchased from Wako Pure Chemical Industries, Ltd. It was distilled before use. Sodium methoxide was purchased from Wako Pure Chemical Industries, Ltd. and was used as received. Diphenyl H-phosphonate was purchased from Wako Pure Chemical Industries, Ltd. with, a purity of 85%, containing <15% phenol. Phenol was removed by distillation before use. 1-Tetradecanol Mw = 214.30 g/mol, 1-hexadecanol Mw = 242.44 g/mol, 1-octadecanol Mw = 270.49 g/mol were purchased from Wako Pure Chemical Industries, Ltd. Trichloroisocianuric acid, 97% (TCIA) Sigma-Aldrich (St. Louis, MO, USA).

Oleic acid (FA 18:1), trioleoyl glycerol (TG 18:1/18:1/18:1), pyridinium p-toluenesulfonate (PPTS), trioctanoyl glycerol (TG 8:0/8:0/8:0) and deuterated methanol (CH₃OD) (99.5 atom % D) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Dioleoyl glycerol (DG 18:1/18:1/0:0), 2-methoxypropene (MxP), N,N′-dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), 2, 2′-azobis (4-methoxy-2, 4-dimethylvaleronitrile) (MeO-AMVN), fatty acid-free bovine serum albumin and sodium methoxide were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Boron trifluoride diethyl ether complex was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Oleic acid methyl ester (FA 18:1; 1OMe) was purchased from Nu-Chek Prep Inc. (Elysian, MN). α-Lipase (neurase F3G) was kindly provided by Amano Enzyme Inc. (Aichi, Japan). Sodium taurocholate was purchased from Nacalai Tesque, Inc. (Kyoto, Japan). All other reagents were of analytical grade or higher.