Preparation and Molecular Recognition Ability of Mono[6-deoxy-6-( l -tyrosylamino)]-β-cyclodextrin. Formation and Guest Binding Properties of Distorted Cavity Formed Outside the Parent Cyclodextrin

Mono[6-deoxy-6-(l-tyrosylamino)]-β-cyclodextrin (2) was prepared from N-(benzylcarbonyl)-l-tyrosine dicyclohexylamine salt (Z-Tyr DCHA salt) and mono(6-amino-6-deoxy)-β-cyclodextrin. 2 includes N-dansylphenylalanine enantioselectively (KL/KD = 2.13). From an NMR study, it was suggested that the hydroxyphenyl group attached to 2 was located at the outside of the cavity and that 2 had an expanded and distorted cavity enclosed by the hydroxyphenyl moiety and the parent cyclodextrin wall.