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

作者：Hakamata Wataru^*; Koyama Ryosuke; Tanida Mizuki; Haga Tomomi; Hirano Takako; Akao Makoto; Kumagai Hitomi; Nishio Toshiyuki

来源：Journal of Agricultural and Food Chemistry, 2015, 63(50): 10778-10784.

DOI：10.1021/acs.jafc.5b05501

• absolute configuration
• alliin
• allo-alliin
• diastereoselective
• garlic
• synthesis
• X-ray crystallography

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 dichroisrn 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 H-1 NMR spectrum was observed for synthetic and natural alum. The absolute configuration of natural alliin was assigned for the first time on the basis of the NMR spectrum and X-ray coordinates.

• 出版日期2015-12-23