Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction
Glycopolymers have gained increasing importance in investigating glycan-lectin interactions, as drug delivery vehicles and in modulating interactions with proteins. The synthesis of these glycopolymers is still a challenging and rigorous exercise. In this regard, the highly efficient click reaction,...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/24/1/157 |
| _version_ | 1818032122543210496 |
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| author | William Ndugire Bin Wu Mingdi Yan |
| author_facet | William Ndugire Bin Wu Mingdi Yan |
| author_sort | William Ndugire |
| collection | DOAJ |
| description | Glycopolymers have gained increasing importance in investigating glycan-lectin interactions, as drug delivery vehicles and in modulating interactions with proteins. The synthesis of these glycopolymers is still a challenging and rigorous exercise. In this regard, the highly efficient click reaction, copper (I)-catalyzed alkyne-azide cycloaddition, has been widely applied not only for its efficiency but also for its tolerance of the appended carbohydrate groups. However, a significant drawback of this method is the use of the heavy metal catalyst which is difficult to remove completely, and ultimately toxic to biological systems. In this work, we present the synthesis of carbohydrate-grafted glycopolymers utilizing a mild and catalyst-free perfluorophenyl azide (PFPA)-mediated Staudinger reaction. Using this strategy, mannose (Man) and maltoheptaose (MH) were grafted onto the biodegradable poly(lactic acid) (PLA) by stirring a PFAA-functionalized PLA with a phosphine-derivatized Man or MH in DMSO at room temperature within an hour. The glycopolymers were characterized by 1H-NMR, 19F-NMR, 31P-NMR and FTIR. |
| first_indexed | 2024-12-10T06:02:21Z |
| format | Article |
| id | doaj.art-ed410faf15f44705b83d3d536ca7e294 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T06:02:21Z |
| publishDate | 2019-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ed410faf15f44705b83d3d536ca7e2942022-12-22T01:59:48ZengMDPI AGMolecules1420-30492019-01-0124115710.3390/molecules24010157molecules24010157Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger ReactionWilliam Ndugire0Bin Wu1Mingdi Yan2Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, USADepartment of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, USADepartment of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, USAGlycopolymers have gained increasing importance in investigating glycan-lectin interactions, as drug delivery vehicles and in modulating interactions with proteins. The synthesis of these glycopolymers is still a challenging and rigorous exercise. In this regard, the highly efficient click reaction, copper (I)-catalyzed alkyne-azide cycloaddition, has been widely applied not only for its efficiency but also for its tolerance of the appended carbohydrate groups. However, a significant drawback of this method is the use of the heavy metal catalyst which is difficult to remove completely, and ultimately toxic to biological systems. In this work, we present the synthesis of carbohydrate-grafted glycopolymers utilizing a mild and catalyst-free perfluorophenyl azide (PFPA)-mediated Staudinger reaction. Using this strategy, mannose (Man) and maltoheptaose (MH) were grafted onto the biodegradable poly(lactic acid) (PLA) by stirring a PFAA-functionalized PLA with a phosphine-derivatized Man or MH in DMSO at room temperature within an hour. The glycopolymers were characterized by 1H-NMR, 19F-NMR, 31P-NMR and FTIR.http://www.mdpi.com/1420-3049/24/1/157Glycopolymerpost-polymerization functionalizationperfluoroaryl azidesStaudinger reaction |
| spellingShingle | William Ndugire Bin Wu Mingdi Yan Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction Molecules Glycopolymer post-polymerization functionalization perfluoroaryl azides Staudinger reaction |
| title | Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction |
| title_full | Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction |
| title_fullStr | Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction |
| title_full_unstemmed | Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction |
| title_short | Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction |
| title_sort | synthesis of carbohydrate grafted glycopolymers using a catalyst free perfluoroarylazide mediated fast staudinger reaction |
| topic | Glycopolymer post-polymerization functionalization perfluoroaryl azides Staudinger reaction |
| url | http://www.mdpi.com/1420-3049/24/1/157 |
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