Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis

Org Lett. 2019 Apr 5;21(7):2241-2245. doi: 10.1021/acs.orglett.9b00524. Epub 2019 Mar 8.

Abstract

A highly regio-specific and donor-promiscuous 3- O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3- O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3- O-glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / metabolism*
  • Glycosides / chemistry*
  • Glycosylation
  • Glycosyltransferases / chemistry
  • Glycosyltransferases / isolation & purification
  • Glycosyltransferases / metabolism*
  • Models, Molecular
  • Molecular Structure
  • Scutellaria baicalensis / chemistry*

Substances

  • Flavonoids
  • Glycosides
  • Glycosyltransferases