Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions
Dioxolenium ion intermediates formed from remote positions are hypothesized to direct stereoselective glycosylations. Herein we combine infrared ion spectroscopy, DFT calculations and synthetic work to characterize and study these dioxolenium ions and their role in stereoselective glycosylation reac...
| Main Authors: | , , , , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2020-05-01
|
| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-020-16362-x |
| _version_ | 1818855463547043840 |
|---|---|
| author | Thomas Hansen Hidde Elferink Jacob M. A. van Hengst Kas J. Houthuijs Wouter A. Remmerswaal Alexandra Kromm Giel Berden Stefan van der Vorm Anouk M. Rijs Hermen S. Overkleeft Dmitri V. Filippov Floris P. J. T. Rutjes Gijsbert A. van der Marel Jonathan Martens Jos Oomens Jeroen D. C. Codée Thomas J. Boltje |
| author_facet | Thomas Hansen Hidde Elferink Jacob M. A. van Hengst Kas J. Houthuijs Wouter A. Remmerswaal Alexandra Kromm Giel Berden Stefan van der Vorm Anouk M. Rijs Hermen S. Overkleeft Dmitri V. Filippov Floris P. J. T. Rutjes Gijsbert A. van der Marel Jonathan Martens Jos Oomens Jeroen D. C. Codée Thomas J. Boltje |
| author_sort | Thomas Hansen |
| collection | DOAJ |
| description | Dioxolenium ion intermediates formed from remote positions are hypothesized to direct stereoselective glycosylations. Herein we combine infrared ion spectroscopy, DFT calculations and synthetic work to characterize and study these dioxolenium ions and their role in stereoselective glycosylation reactions. |
| first_indexed | 2024-12-19T08:09:00Z |
| format | Article |
| id | doaj.art-6ec49b5d3eff4a6ea8a8b5a70ecb1904 |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-12-19T08:09:00Z |
| publishDate | 2020-05-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-6ec49b5d3eff4a6ea8a8b5a70ecb19042022-12-21T20:29:41ZengNature PortfolioNature Communications2041-17232020-05-011111910.1038/s41467-020-16362-xCharacterization of glycosyl dioxolenium ions and their role in glycosylation reactionsThomas Hansen0Hidde Elferink1Jacob M. A. van Hengst2Kas J. Houthuijs3Wouter A. Remmerswaal4Alexandra Kromm5Giel Berden6Stefan van der Vorm7Anouk M. Rijs8Hermen S. Overkleeft9Dmitri V. Filippov10Floris P. J. T. Rutjes11Gijsbert A. van der Marel12Jonathan Martens13Jos Oomens14Jeroen D. C. Codée15Thomas J. Boltje16Leiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and MaterialsLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and MaterialsLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and MaterialsRadboud University Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7-cLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7-cLeiden University, Leiden Institute of ChemistryLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and MaterialsLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7-cRadboud University Institute for Molecules and Materials, FELIX Laboratory, Toernooiveld 7-cLeiden University, Leiden Institute of ChemistryRadboud University Institute for Molecules and MaterialsDioxolenium ion intermediates formed from remote positions are hypothesized to direct stereoselective glycosylations. Herein we combine infrared ion spectroscopy, DFT calculations and synthetic work to characterize and study these dioxolenium ions and their role in stereoselective glycosylation reactions.https://doi.org/10.1038/s41467-020-16362-x |
| spellingShingle | Thomas Hansen Hidde Elferink Jacob M. A. van Hengst Kas J. Houthuijs Wouter A. Remmerswaal Alexandra Kromm Giel Berden Stefan van der Vorm Anouk M. Rijs Hermen S. Overkleeft Dmitri V. Filippov Floris P. J. T. Rutjes Gijsbert A. van der Marel Jonathan Martens Jos Oomens Jeroen D. C. Codée Thomas J. Boltje Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions Nature Communications |
| title | Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| title_full | Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| title_fullStr | Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| title_full_unstemmed | Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| title_short | Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| title_sort | characterization of glycosyl dioxolenium ions and their role in glycosylation reactions |
| url | https://doi.org/10.1038/s41467-020-16362-x |
| work_keys_str_mv | AT thomashansen characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT hiddeelferink characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT jacobmavanhengst characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT kasjhouthuijs characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT wouteraremmerswaal characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT alexandrakromm characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT gielberden characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT stefanvandervorm characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT anoukmrijs characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT hermensoverkleeft characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT dmitrivfilippov characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT florispjtrutjes characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT gijsbertavandermarel characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT jonathanmartens characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT josoomens characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT jeroendccodee characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions AT thomasjboltje characterizationofglycosyldioxoleniumionsandtheirroleinglycosylationreactions |