LAUSR

A series of mannose-templated microgels with immobilized catalytic sites and catalysis-supporting co-monomers was synthesized and evaluated for catalytic hydrolyses of glycosidic bonds. Interactions of the secondary coordination sphere around the catalytic center were implemented between the sugar and surrounding monomers by copolymerization of corresponding acrylates. The obtained microgels were evaluated for their ability to enhance the catalytic hydrolysis of glycosidic bonds in neutral and alkaline solution. The catalytic proficiency of the microgels reaches a remarkable value of 1.4 × 107 at neutral pH when hydrogen-bond-accepting 2-methoxyethyl acrylate is embedded in 20 mol % as a co-monomer, instead of butyl acrylate. The results indicate a strong influence of hydrogen-bond-accepting co-monomers on the stability of the transition state of glycoside hydrolyses in the designed biomimetic catalysts. The overall performance of all microgels correlates very well with the calculated dipole moments of th...