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Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction

Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, USA
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Molecules 2019, 24(1), 157; https://doi.org/10.3390/molecules24010157
Received: 5 December 2018 / Revised: 28 December 2018 / Accepted: 30 December 2018 / Published: 3 January 2019
(This article belongs to the Special Issue Smart and Functional Polymers)
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Abstract

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. View Full-Text
Keywords: Glycopolymer; post-polymerization functionalization; perfluoroaryl azides; Staudinger reaction Glycopolymer; post-polymerization functionalization; perfluoroaryl azides; Staudinger reaction
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Ndugire, W.; Wu, B.; Yan, M. Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction. Molecules 2019, 24, 157.

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