Glucosylation of benzyl alcohols by the cultured suspension cells of Nicotiana tabacum and Catharanthus roseus |
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Affiliation: | 1. Department of Chemistry, Faculty of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi, Hiroshima 739-8526, Japan;2. Instrument Center for Chemical Analysis, Hiroshima University, 1-3-1 Kagamiyama, Higashi, Hiroshima 739-8526, Japan;3. Department of Chemistry, Kyungnam University, 449 Wolyoung-Long, Masan 631-701, South Korea;1. Graduate School of Sciences and Technology for Innovation (Agriculture), Department of Biological Chemistry, Yamaguchi University, Yamaguchi, Japan;2. Kyoto Institute of Technology, Matsugasaki Sakyo-ku, Kyoto, Japan;3. Research Institute of Green Science and Technology, Shizuoka University, Shizuoka, Japan |
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Abstract: | The cultured cells of Nicotiana tabacum (white cells) converted regioselectively exogenous 2-, 3-, and 4-hydroxybenzyl alcohols into corresponding hydroxybenzyl-β-d-glucopyranoside. (RS)-1-Phenylethanol having chiral center in its substituent was also glucosylated to give 1-phenylethyl-β-d-glucopyranoside by the cultured cells of N. tabacum (white and green cells) and Catharanthus roseus. The glucosylation with the green cells of N. tabacum occurred enantioselectively to give the glucoside of (S)-alcohol preferentially, while the glucosylation with the white cells of N. tabacum and the C. roseus cells gave preferentially the glucoside of (R)-alcohol. |
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