Determination of optical purity and absolute configuration of natural 12‐hydroxystearic acid by the 1H NMR anisotropy method |
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| Authors: | Satoshi Murakami Kazuhiro Satou Taturo Kijima Masataka Watanabe Taeko Izumi |
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| Affiliation: | Graduate School of Science and Engineering, Yamagata University, Jyonan, Yonezawa, Japan |
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| Abstract: | The enantiopure of (R)‐(?) MαNPA was allowed to react with racemic 18‐(tert‐butyldimethylsilyloxy)‐5‐octadecayne‐7‐ol which was derived from dodecane‐1,12‐diol, yielding diastereomeric esters mixture. These racemic esters were easily separated by HPLC on silica‐gel. The absolute configurations of the first‐eluted diastereomeric esters from the separated esters were determined using 1H NMR anisotropy method. Analysis on 1H NMR spectra and HPLC elution time of the synthesized esters and those of MαNP ester derived from natural methyl‐12‐hydroxystealate showed that the absolute configuration of natural 12‐hydroxystearic acid was R form, and the enantiomeric excess was over 99%. |
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| Keywords: | Absolute configuration Anisotropy method Chiral 12‐Hydroxystearic acid NMR |
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