Preparation of a new pepper: chemoenzymatic synthesis of capsaicin oligosaccharide and 8-nordihydrocapsaicin oligosaccharide

Capsaicin and 8-nordihydrocapsaicin were readily converted into the corresponding monoglucosides (capsaicin β-d-glucopyranoside and 8-nordihydrocapsaicin β-d-glucopyranoside) with tetraacetyl-α-d-glucose fluoride (TAGF) in the presence of BF3·OEt2. Furthermore, capsaicin oligosaccharides and 8-nordihydrocapsaicin oligosaccharides were synthesized from their monoglucosides by a cyclodextrin glucanotransferase (CGTase)-catalyzed glycosylation for the preparation of higher water-soluble capsaicinoids.