Abstract: The influence of the binding group flexibility on the ability for racemic resolution was investigated for binding groups situated in chiral cavities of enzyme-analogously built polymers. D-Glyceric acid was used as a template to introduce dihydroxyborylphenyl-, 4-(2-hydroxyborylethyl)phenyl-, or 5-dihydroxyboryl-1,2-indanediyl groups into chiral cavities of macroporous polymers. Investigations on the ability for racemic resolution revealed a lower specificity with higher binding group flexibility. On increasing the rigidity compared to the dihydroxyborylphenyl group the specificity is diminished to some extent. This may be attributable to a hindrance of the embedding of the substrate

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