95(P-6) 分岐アルキル鎖の遠隔位不斉識別法の開発と天然化合物の絶対配置決定への応用(ポスター発表の部)

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Recently, we have been reported (1S,2S)-2-(2,3-anthracenedicarboximido)cyclohexanol (1) as a highly sensitive chiral fluorescent derivatization reagent, which made it possible to separate the enantiomers of carboxylic acids having asymmetric centers at remote positions from their carboxyl group. With the reagent, diastereomeric derivatives of chiral anteiso fatty acids having chiral centers from 2 to 12 position were separated into two peaks by reversed-phase HPLC using an ODS column and detected at the femto mole levels by fluorometry. Here, we report the HPLC separation of chiral anteiso fatty acids having chiral centers from 13 to 18 position and the applications to the determination of the absolute configurations of chiral branched fatty acids derived from natural products. The anteiso fatty acids having chiral centers at from 13 to 18 position were prepared from (S)-4-methylhexanol or (S)-2-methylbutanol. The authentic derivatives of (S,S)- and (R,R)-1, were prepared by using 1-ethyl-3-(3-dimethylami nopropyl)carbodiimide and 4-dimethylaminopyridine, and they were separated into two peaks with more than 0.57 of Rs value by a reversed-phase HPLC under very low flow rate (0.1〜0.4ml/min) and column temperature (-50〜-40℃) conditions (Table). The method was successfully applied to determine the absolute configuration of branched fatty acid moiety of a nobel glycoglycerolipid, S365A(9), isolated from Corynebacyerium aquatic. The S365 have 12-methyltetradecanoic and 14-methylh exadecaoic acid moieties and both of them were determined by the proposed method to be S. 2-(Anthraceneimido)cyclohexane carboxylic acxid (12) was also synthesized as a chiral derivatization reagent for alcohols. After derivatization with 12, the chiral praimary and secondary alcohols were successfully discriminated by ^1H-NMR. Moreover, their enatiomeric separation was also possible by a reversed-phase HPLC under very low column temperature and flow rate.
2000-10-01

95(P-6) 分岐アルキル鎖の遠隔位不斉識別法の開発と天然化合物の絶対配置決定への応用(ポスター発表の部)

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