Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach

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.

Glycopolymer Based LbL Multilayer Thin Films with Embedded Liposomes

“…The procedure is adapted and modified from previous publications. [ 35,36 ] First, a glycosylamine is formed from the starting material via microwave‐assisted Kochetkov amination, followed by the conversion to a methacrylamide (MAm) which constitutes our final glycomonomers GalNAcMAm and LacMAm. We confirmed the formation of glycomonomers via NMR spectroscopy.…”

“…LacMAm and both glycosylamines have been characterized in previous studies. [35,36] The respective glycomonomer is polymerized by a thermally initiated, free radical polymerization in water. We utilized 1 H NMR spectroscopy to verify the glycopolymers and to investigate the conversion and polymerization kinetic of glycomonomers.…”

Microwave-Assisted Synthesis of 5′-O-methacryloylcytidine Using the Immobilized Lipase Novozym 435

“…Over the last 30 years, the application of microwave irradiation to chemical reactions has increased significantly. It is used in organic [17][18][19] and organometallic synthesis [20,21], inorganic solid-state reactions [22], catalysis and even peptide synthesis [23,24], polymer chemistry or nanotechnology [25]. Due to the steady heat distribution, the yield in organic syntheses can be increased in a reduced reaction time compared to conventional heating with an oil bath.…”