Exploring the glycosylation capabilities of Gliocladium deliquescens NRRL 1086 on hydroxyl benzophenones

• Glycosides of hydroxylated benzophenones were synthesized through microbial transformation.
• One step and high efficient glycosylation culture was applied.
• Regio-selectivity was investigated.
• Substrate scope of the unique microbe of Gliocladium deliquescens NRRL 1086 was expanded.

This study explored the substrate scope and regio-selectivity of Gliocladium deliquescens NRRL 1086 on hydroxylated benzophenones (HBPs), which was the follow-up investigation on the glycosylation of phenolic hydroxyl compounds by this unique microbe. Five HBPs substrates were used and three glycosylated metabolites, iriflophenone 2-O-β-d-glycopyranoside (6, 40%), riflophenone 4-O-β-d-glycopyranoside(7, 21%) and 2,6,4′-trihydroxy-4-methoxybenzophenone-2-O-β-d-glycopyranoside (8, 65%) were isolated and structurally identified unambiguously by ESI-MS, 1H NMR, 13C NMR, and 2D NMR spectroscopy. The versatile glycosylation ability of G. deliquescens NRRL 1086 on phenolic hydroxyl compounds may provide an alternative and convenient method to enable high-efficiency synthesis of various HBPs glycosides.

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