Adipic acid

Isobutyl chloroformate (≥98.0%), 4-carboxyphenylboronic acid (≥97.0%), 4-methylmorpholine (≥99.0%), (R)-(-)-2-phenylpropionic acid (≥98.0%), and (S)-(+)-2-phenylpropionic acid (≥98.0%) were purchased from Tokyo Chemical Industry Co., Ltd. (TCI, Tokyo, Japan). Bicyclo [2.2.1]hepta-2,5-diene-rhodium(I) chloride dimer (Rh (nbd)Cl₂, ≥96%), propargylamine (≥98.0%), propargyl alcohol, and sodium tetraphenylboron were obtained from Sigma–Aldrich (St Louis, MO, United States). α-D- and α-L-Glucose were purchased from Thermo Fisher Scientific (Geel, Belgium). Anhydrous magnesium sulfate (MgSO₄), benzene, sodium chloride (NaCl), sodium hydrogen carbonate (NaHCO₃), 2 mol L⁻¹ hydrochloric acid (HCl), p-toluenesulfonic acid monohydrate, super dehydrated tetrahydrofuran (THF), super dehydrated methanol (CH₃OH), chloroform (CHCl₃), and potassium bromide (KBr, infrared (IR) grade) were purchased from Wako Pure Chemical Industries, Ltd. (Wako, Osaka, Japan). Adipic acid (≥99.5%) and other solvents (tetrahydrofuran, 2-propanol, acetic ether, and ethanol) were acquired from Nacalai Tesque, Inc. (Kyoto, Japan).

Methoxyamine hydrochloride (quality level: MQ 200) was purchased from Merck (Darmstadt, Germany). Pyridine (extra dry) (99.5+% evaluated by capillary GC), acetone (Dioxins Analysis Grade, purity 99.8%), and d₁₀-phenanthrene (Environment Analysis Grade, purity 99.5%) were obtained from Wako Chemicals Ltd. (Osaka, Japan). The metabolite mixture kit for GC/MS-based metabolomics and N-methyl-N-(trimethylsilyl trifluoroacetamide) (MSTFA) were purchased from GL Sciences Inc. (Tokyo, Japan). Acetonitrile (LC-MS grade) and methanol (LC-MS grade) were purchased from Kanto Chemical (Tokyo, Japan). Standard Reference Material (SRM) 1950 “Metabolites in Human Plasma” was obtained from the National Institute of Standards and Technology (NIST, Gaithersburg, MD). Adipic acid (purity 99.5%), chloroform (purity 99.0%), and methanol (purity 99.8%) were obtained from Nacalai Tesque Inc. (Kyoto, Japan).