AbstractThe chemoenzymatic synthesis of new side‐chain polyrotaxanes (6) bearing non‐covalently attached cyclodextrins is described. Starting from 11‐methacryloylaminoundecanoic acid, up to 8 units of 12‐hydroxylauric acid were condensed in the presence of a lipase fromCandida antarctica. They were copolymerized with methyl methacrylate to comb‐like polymers (4) bearing free carboxylic groups at the end of the oligoester side chains. These free carboxylic groups were then condensed chemically with a nucleophilic barrier group,N‐(4‐aminobutanoyl)‐4‐triphenylmethylaniline (5), in the presence of dimethylated β‐cyclodextrin, yielding new polyrotaxanes that contain statistically more than 1 ring comp