title: A Simple Synthesis of Alliin and allo-Alliin: X-ray Diffraction Analysis and Determination of Their Absolute Configurations.
abstract: 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 (1)H 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.
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Hakamata
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Koyama
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Mizuki
authors.initials: M
authors.lastname: Tanida
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Tomomi
authors.initials: T
authors.lastname: Haga
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Takako
authors.initials: T
authors.lastname: Hirano
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Akao
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Hitomi
authors.initials: H
authors.lastname: Kumagai
authors.affiliation: Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University , 1866 Kameino, Fujisawa-shi, Kanagawa 252-0880, Japan.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Nishio
mesh_terms: D002942:Circular Dichroism; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005737:Garlic / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D013455:Sulfur; C006453:alliin; D003545:Cysteine
keywords: X-ray crystallography; absolute configuration; alliin; allo-alliin; diastereoselective; garlic; synthesis