Enzyme‐analogue built polymers, 29. The preparation of defined chiral cavities for the racemic resolution of free sugars

Abstract

Abstract New types of macroporous polymers containing chiral cavities were prepared for the racemic resolution of free sugars. As template monomers 6‐ O ‐methyl‐ and 6‐ O ‐benzyl‐α D ‐galactopyranose 1,2;3,4‐tetra‐ O ‐bis(4‐vinylphenylboronate) ( 3c and b ) as well as 1‐ O ‐methyl‐ and 1‐ O ‐benzyl‐β D ‐fructopyranose 2,3;4,5‐tetra‐ O ‐bis(4‐vinylphenylboronate) ( 4c and b ) were copolymerized with a large amount of ethylene dimethacrylate. After splitting off the respective templates, these polymers were used for the racemic resolution of the racemates of D , L ‐galactose and D , L ‐fructose, and also the racemates, of 1‐ O ‐methyl‐ and 1‐ O ‐benzyl‐ D , L ‐fructose. The polymer prepared from 3b yielded the highest selectivity for the racemic resolution of D , L ‐galactose. In the case of fructose the benzyl‐ether‐imprinted polymers yielded the highest selectivity, especially for 1‐ O ‐methyl‐ D , L ‐fructose separation. Polymers imprinted with D ‐galactose derivatives showed inverse selectivity by preferably absorbing L ‐fructose from the racemate. Polymerization at lower temperatures usually yielded more selective polymers.