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Regioselective glycosylation of novobiocin alters activity

Sun, G; de Resende, PE; Stapleton, P; Kuta, M; Wang, X; Haider, S; Yang, M; (2017) Regioselective glycosylation of novobiocin alters activity. Carbohydrate Research , 452 pp. 116-121. 10.1016/j.carres.2017.10.011. Green open access

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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.

Type: Article
Title: Regioselective glycosylation of novobiocin alters activity
Location: Netherlands
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.carres.2017.10.011
Publisher version: https://doi.org/10.1016/j.carres.2017.10.011
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Antibacterial activity, Glycosylation, Novobiocin, Phase transfer reaction
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > SoP Pharmaceutical and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10033917
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