jo9b00830_si_001.pdf (8.69 MB)
Conformationally Switchable Glycosyl Donors
journal contribution
posted on 2019-10-18, 15:04 authored by Thomas Holmstrøm, Christian Marcus PedersenGlycosyl
donors functionalized with 2,2′-bipyridine moieties
on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational
change when forming 1:1 complexes with Zn2+ ions. The pyranoside
ring of the zinc complexes adopted axial-rich skew boat conformations.
The reactivities of the two glycosyl donors were investigated by performing
a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when
binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable
to undergo conformational changes when binding Zn2+. From
competition experiments, it was observed that the binding-induced
conformational change increased the reactivity slightly compared to
the glycosyl donor unable to undergo a conformational change.