Molecular Recognition: α-Cyclodextrin and Penicillin V Inclusion Complexation

Article abstract of DOI:10.1021/jo00004a037

Specific molecular recognition between α-cyclodextrin (1) and a β-lactam antibiotic, penicillin V (2), was systematically determined.A stable 1:1 inclusion complex was established in the solid state, gaseous phase, and solution.The distinct structure of this inclusion complex was rigorously elucidated by FT-IR, FAB-MS, CP/MAS solid state ¹³C NMR, and 500-MHz ¹H NMR.Based on strictly determined ¹H NMR data, a time-averaged conformation of the α-CD-penicillin V inclusion complex was proposed, which was supported by CPK model studies and the intermolecular NOE results.Moreover, α-cyclodextrin exhibited significant catalytic activity toward the hydrolysis of penicillin V in weakly alkyline solution.These findings imply that the initial molecular recognition and the concomitant molecular association are essential in a biomimetic process.