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Preparation of cruciferous phytoalexin related metabolites, (−)-dioxibrassinin and (−)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD) |
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| Authors: | Kenji Monde Tohru TaniguchiNobuaki Miura Shin-Ichiro Nishimura Nobuyuki HaradaRina K Dukor Laurence A Nafie |
| Affiliation: | a Laboratory for Bio-Macromolecular Chemistry, Division of Biological Sciences, Graduate School of Science, Frontier Research Center for Post-genomic Science and Technology, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan b Sapporo Laboratory for Glycocluster Project, Japan Bioindustry Association, Sapporo 001-0021, Japan c Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba, Sendai 980-8577, Japan d BioTools Inc., 950 N. Rand Road Unit, 123, Wauconda, IL 60084, USA e Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, USA |
| Abstract: | Cruciferous phytoalexin related metabolites, (−)-dioxibrassinin (1) and (−)-3-cyanomethyl-3-hydroxyoxindole (2) were prepared from isatin as racemates and were resolved by chiral HPLC. Their absolute configurations were determined by the new chiroptical technique, vibrational circular dichroism (VCD), as well as by the conventional electronic circular dichroism (ECD). It is concluded that the absolute configurations of the naturally occurring (−)-1 and (−)-2 are both S. |
| Keywords: | VCD dioxindole dioxibrassinin phytoalexin tertiary alcohol |
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