Dec, 2015
A Simple Synthesis of Alliin and allo-Alliin: X-ray Diffraction Analysis and Determination of Their Absolute Configurations
Journal of Agricultural and Food Chemistry
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- Volume
- 63
- Number
- 50
- First page
- 10778
- Last page
- 10784
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1021/acs.jafc.5b05501
- Publisher
- AMER CHEMICAL SOC
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.
- Link information
- ID information
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- DOI : 10.1021/acs.jafc.5b05501
- ISSN : 0021-8561
- eISSN : 1520-5118
- Web of Science ID : WOS:000367561400006