Synthesis of novel saccharide-acrylate monomers using biocatalytic approaches

PhD ceremony: Mr. W.M.J. Kloosterman, 14.30 uur, Academiegebouw, Broerstraat 5, Groningen

Dissertation: Synthesis of novel saccharide-acrylate monomers using biocatalytic approaches

Promotor(s): prof. K. Loos

Faculty: Mathematics and Natural Sciences

Polyacrylates with pending saccharide groups (poly saccharide-acrylates) combine the properties of saccharides with the hydrophobic properties of polyacrylates. The polymers are synthesized from monofunctionalized saccharide-acrylates. The synthesis of these saccharide-acrylates is difficult or even impossible by conventional synthesis routes, because the saccharides possess multiple hydroxyl groups with more less the same reactivity. Using biocatalysts on the other hand, has the advantage of high selectivity towards the bond formation.

The goal of this PhD research is to find biocatalytic approaches that can be used for the synthesis of monofunctional saccharide-acrylates.

Several enzymes of the glycosyl-hydrolase family are found to catalyze the reaction between hydroxyl functional acrylates and saccharides. The saccharide residues are obtained from cheap raw materials, like starch and cellulose (cotton).

As a result of the high selectivity of the enzymes used, the saccharide-acrylates contain only one acrylate group per saccharide. Furthermore, the selection of the appropriate enzyme can result in saccharide-acrylates containing one glucose group, one maltose group (two glucose residues) or a mixture of one to fourteen glucose residues.

Since the saccharide-acrylates contain only one functional group per saccharide, they can successfully be polymerized using (environmentally friendly) aqueous free radical polymerization in water. The resulting poly(saccharide-acrylates) are soluble in water. In the future, the novel kind of polymers can be used in applications like for instance dispersing agents in cosmetics, drug carriers and other biomedical applications.