Regioselective glycosylation of novobiocin alters activity

Guoxuan Sun, Pedro Ernesto de Resende, Paul Stapleton, Martyna Kuta, Xiangtao Wang, Shozeb Haider, Min Yang

Research output: Contribution to journalArticlepeer-review

Abstract

Glycosylation is a promising approach to overcome antimicrobial drug resistance. In this study, we investigated Koenigs-Knorr and phase transfer glycosylation on novobiocin. While the former only gave a 4′-OH product, the later produced mainly a kinetic controlled 5-OH product, but still achieved the 4′-OH modification and novoise-glycosylated products (with stronger base), as well as a diglycosylated compound. Investigation on the antibacterial activity indicate that the presence of galactose moiety helps to improve activity possibly via enhanced cellular uptake.
Original languageEnglish
Pages (from-to)116-121
Number of pages6
JournalCarbohydrate Research
Volume452
Early online date22 Oct 2017
DOIs
Publication statusPublished - 27 Nov 2017

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