Abstract
Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regioselective amination conditions of different saccharides. Amination reactions were performed according to Kochetkov and Likhoshertov and accelerated by microwave irradiation. We optimized the synthesis of glycosylamines for N-acetyl-d-galactosamine, d-lactose, d-glucuronic acid and l-(−)-fucose using the design of experiments (DoE) approach. DoE enables efficient optimization with limited number of experimental data. A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. There is strong indication that high temperatures are favored for the amination reaction.
Highlights
Glycosylation is a crucial modification of biomolecules involved in almost all biological processes [1,2,3,4,5]
We optimized the synthesis of glycosylamines for N-acetyl-d-galactosamine, d-lactose, d-glucuronic acid and l-(−)-fucose using the design of experiments (DoE) approach
We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature
Summary
Glycosylation is a crucial modification of biomolecules involved in almost all biological processes [1,2,3,4,5]. The glycans may be chemically modified and presented in polymers [15,16,17], on surfaces [18,19,20,21,22], on nanoparticles [23,24,25] or as (multivalent) glycan derivatives [26,27,28,29] with increased binding affinity [30,31,32] Prerequisites for this are straight forward chemical processes that yield regioselective modifications of glycans without hampering the natural recognition processes. We utilized a protecting group free process to regioselectively insert an amino group into saccharides at the
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