Synthesis of Ceramides Bearing DL-<I>erythro</I>- and DL-<I>threo</I>-C<SUB>n</SUB>-Dihydrosphingosines, and the Determination of the <I>erythro</I> and <I>threo</I> Isomers by Mass Spectrometry

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  • DL-<I>erythro</I>-及びDL-<I>threo</I>-C<SUB>n</SUB>-ジヒドロスフィンゴシンを骨格に有するセラミドの合成と質量分析法によるそれらの<I>erythro</I>及び<I>threo</I>の決定法
  • DL erythro オヨビ DL threo Cn ジヒ

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DL-threo- and DL-erythro-Cn-dihydrosphingosines (n=12, 14, and 16) were separated from the corresponding 2-amino-1, 3-alkanediols by repeated recrystallization of the N, O, O-triacetyl and N-acetyl derivatives. Ceramides having DL-threo- and DL-erythro-Cn-dihydrosphingosines were prepared by reactions of the bases with N-acyloxysuccinimides in tetrahydrofuran. GLC-MS analysis of O, O-di-TMS derivatives of the ceramides was carried out to find differences between threo and erythro isomers in mass spectra. One characteristic difference was observed in the relative intensity (RI) at m/e=M-103; i.e., the relative intensities of threo compounds (RI 4080%) were stronger than those of erythro isomers (RI 614%). The ratios, RI(M-103)/RI(M-15), were 3.76.8 and 0.81.3 for threo and erythro compounds, respectively. These observations demonstrate the possibility of determining erythro and threo isomers by mass spectrometry.

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