A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities
Alexander Gutmann1, Corinna Krump, Linda Bungaruang
1Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12/1, A-8010 Graz, Austria. bernd.nidetzky@tugraz.at.
None:
An efficient 2'-O- to 3'-C-β-d-glucosidic bond rearrangement on the dihydrochalcone phloretin to convert phlorizin into nothofagin was achieved by combining complementary O-glycosyltransferase (OGT) and C-glycosyltransferase (CGT) activities in a one-pot transformation containing catalytic amounts of uridine 5'-diphosphate (UDP). Two separate enzymes or a single engineered dual-specific O/CGT were applied. Overall (quantitative) conversion occurred in two steps via intermediary UDP-glucose and phloretin.
Related Concept Videos
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
C–C Bond Formation: Aldol Condensation Overview
Glycolysis: Preparatory Phase


