Conformationally Switchable Glycosyl Donors

Thomas Holmstrøm; Christian Marcus Pedersen

doi:10.1021/acs.joc.9b00830

Conformationally Switchable Glycosyl Donors

Thomas Holmstrøm, Christian Marcus Pedersen

Department of Chemistry

3 Citations (Scopus)

Abstract

Glycosyl 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.

Original language	English
Journal	The Journal of Organic Chemistry
Volume	84
Issue number	21
Pages (from-to)	13242-13251
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.9b00830
Publication status	Published - 1 Nov 2019

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10.1021/acs.joc.9b00830

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title = "Conformationally Switchable Glycosyl Donors",

abstract = "Glycosyl 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.",

author = "Thomas Holmstr{\o}m and Pedersen, {Christian Marcus}",

year = "2019",

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doi = "10.1021/acs.joc.9b00830",

language = "English",

volume = "84",

pages = "13242--13251",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Conformationally Switchable Glycosyl Donors

AU - Holmstrøm, Thomas

AU - Pedersen, Christian Marcus

PY - 2019/11/1

Y1 - 2019/11/1

N2 - Glycosyl 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.

AB - Glycosyl 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.

U2 - 10.1021/acs.joc.9b00830

DO - 10.1021/acs.joc.9b00830

M3 - Journal article

C2 - 31584274

SN - 0022-3263

VL - 84

SP - 13242

EP - 13251

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Conformationally Switchable Glycosyl Donors

Abstract

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