A Simple Synthesis of Alliin and allo-Alliin: X-ray Diffraction Analysis and Determination of Their Absolute Configurations

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• 作者：Wataru Hakamata ; Ryosuke Koyama ; Mizuki Tanida ; Tomomi Haga ; Takako Hirano ; Makoto Akao ; Hitomi Kumagai ; Toshiyuki Nishio
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2015
• 出版时间：December 23, 2015
• 年：2015
• 卷：63
• 期：50
• 页码：10778-10784
• 全文大小：399K
• ISSN：1520-5118

文摘

A simple method for the isolation of the bioactive compound alliin from garlic, as well as a method for the synthesis of diastereomerically pure alliin and allo-alliin on a preparative laboratory scale, was developed. The absolute configuration of the sulfur atom in alliin and allo-alliin was assigned on the basis of enzyme reactivity, optical rotatory dispersion, and circular dichroism analyses. A comparison of the results from these analyses, in combination with an X-ray diffraction study on a protected allo-alliin derivative, revealed S and R configurations of the sulfur atoms in alliin and allo-alliin, respectively. In addition, the same ¹H NMR spectrum was observed for synthetic and natural alliin. The absolute configuration of natural alliin was assigned for the first time on the basis of the NMR spectrum and X-ray coordinates.