63268-20-2Relevant academic research and scientific papers
Chemical Glucosylation of Labile Natural Products Using a (2-Nitrophenyl)acetyl-Protected Glucosyl Acetimidate Donor
Weber, Julia,Schwarz, Markus,Schiefer, Andrea,Hametner, Christian,H?ubl, Georg,Fr?hlich, Johannes,Mikula, Hannes
, p. 2701 - 2706 (2018)
The synthesis of (2-nitrophenyl)acetyl (NPAc)-protected glucosyl donors is described that were designed for the neighboring-group assisted glucosylation of base-labile natural products also being sensitive to hydrogenolysis. Glycosylation conditions were optimized using a trichloroacetimidate glucosyl donor, and cyclohexylmethanol and (+)-menthol as model acceptors. The approach was then extended to a one-pot procedure for the synthesis of 1,2-trans-glycosides. This method was finally applied for improved synthesis of the masked mycotoxin T2-O-β,d-glucoside.
Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases
Shimoda, Kei,Kubota, Naoji,Hamada, Hiroki
, p. 2319 - 2321 (2007/10/03)
Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C. roseus enantioselectively glucosylated (±)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols.
