Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [H-2(3)]juvenile hormone III as an internal standard for liquid chromatography mass spectrometry quantification

摘要

Juvenile hormone III (JH III) recemate was prepared from methyl (2E,6E)-farnesoate via epoxidation with 3-chloroperbenzoic acid (mCPBA). Enantioselective separation of JH III was conducted using normal-phase high-performance liquid chromatography (HPLC) on a chiral stationary phase. [H-2(3)]Methyl (2E,6E)-farnesoate was also prepared from (2E,6E)-farnesoic acid and [H-2(4)]methanol (methanol-d(4)) using 1-(3dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP); the conjugated double bond underwent isomerization to some degree. Epoxidation of [H-2(3)]methyl (2E,6E)-farnesoate with mCPBA gave a novel deuterium- substituted internal standard [H-2(3)]JH III (JH III-d(3)). The standard curve was produced by linear regression using the peak area ratios of JH III and JH IH-d(3) in liquid chromatography-mass spectrometry (LC-MS). (c) 2007 Elsevier B.V. All rights reserved.