Synthesis of unnatural mono- and oligosaccharides of farnesol, geraniol, and (S)-Perillyl alcohol by biocatalytic glycosylations

Farnesol and geraniol were glucosylated to the corresponding unnatural beta-glucosides, which were two new biotransformation products, by cultured plant cells of Eucalyptus perriniana, Strophanthus gratus, and Phytolacca americana. Cultured E. perriniana cells glycosylated (S)-perillyl alcohol to two beta-glycosides, i.e., beta-glucoside and unnatural beta-gentiobioside, whereas only perillyl beta-glucoside was produced by S. gratus and P. americana. Perillyl beta-glucoside was further converted into two unnatural beta-maltooligosaccharides, i.e., beta-maltoside and beta-maltotrioside, by cyclodextrin glucanotransferase.