TY - JOUR
T1 - Regioselective glycosylation of novobiocin alters activity
AU - Sun, Guoxuan
AU - de Resende, Pedro Ernesto
AU - Stapleton, Paul
AU - Kuta, Martyna
AU - Wang, Xiangtao
AU - Haider, Shozeb
AU - Yang, Min
PY - 2017/11/27
Y1 - 2017/11/27
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-85032288841&partnerID=MN8TOARS
U2 - 10.1016/j.carres.2017.10.011
DO - 10.1016/j.carres.2017.10.011
M3 - Article
SN - 0008-6215
VL - 452
SP - 116
EP - 121
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -