Biospin 400 nmr spectrometers

Optical rotations were determined on a JASCO P-2000 polarimeter (Hachioji, Tokyo, Japan). CD spectra were recorded with a Chirascan spectropolarimeter (Applied Photophysics, Leatherhead, UK). High-resolution electrospray ionization mass spectrometry (ESI-MS) analysis was conducted on an Agilent 6530 Accurate-Mass Q-TOF LC/MS system (Agilent Technologies, Palo Alto, CA, USA). NMR spectra were recorded on Bruker AM600 FT-NMR and Bruker BioSpin 400 NMR spectrometers (Rheinstetten, Germany). Column chromatography (CC) was performed on silica gel (Kiesel gel 60, 70–230 mesh and 230–400 mesh, Merck, Darmstadt, Germany), YMC*GEL (ODS-A, 12 nm S-150 μm, YMC, Kyoto, Japan) and Sephadex LH-20 (Sigma-Aldrich, St. Louis, MO, USA) resins. Precoated silica gel 60 F₂₅₄ (1.05554.0001, Merck, Darmstadt, Germany) and RP-18 F_254S plates (1.15685.0001, Merck) were used for TLC. Preparative high-performance liquid chromatography (HPLC) separations were carried out using a Shimadzu LC-6AD (Shimadzu, Kyoto, Japan) instrument with a YMC-Pack ODS-A column (20 mm I.D. × 250 mm, S-5 μm) and an SPD-20A wavelength detector set at 210 nm.

Optical rotations were determined on a JASCO P-2000 polarimeter (Hachioji, Tokyo, Japan). The CD spectrum was recorded with a Chirascan spectropolarimeter (Applied Photophysics, U.K.). The high-resolution electrospray ionisation mass spectra (ESI-MS) were obtained from an Agilent 6530 Accurate-Mass Q-TOF LC/MS system (CA, U.S.A.). The NMR spectra were recorded on Bruker AM600 FT-NMR and Bruker BioSpin 400 NMR spectrometers (MA, USA). Column chromatography (CC) was performed on silica gel (Kiesel gel 60, 70–230 mesh and 230–400 mesh, Merck, Darmstadt, Germany), YMC*GEL (ODS-A, 12 nm S-150 µm, YMC Co., Ltd., Japan) and Sephadex LH-20 gel (Pharmacia Biotech, Sweden). TLC used pre-coated silica gel 60 F₂₅₄ (1.05554.0001, Merck) and RP-18 F_254S plates (1.15685.0001, Merck, Germany). Preparative high-performance liquid chromatography (HPLC) was carried out using a Shimadzu LC-6AD (Shimadzu, Japan) instrument with a YMC-Pack ODS-A column (20 mm I.D.×250 mm, S-5 µm, 12 nm) and a SPD-20A wavelength detector at 210 nm. Soluble epoxide hydrolases (10011669) and PHOME (10009134) were purchased from Cayman (Cayman, MI, USA).