H-1-NMR STUDY OF CONFORMATION OF FORMYL-L-PHENYLALANYL-6-DEOXY-6-AMINO-CYCLOMALTOHEPTAOSE THAT HAS EXCELLENT ABILITY OF CHIRAL RECOGNITION

N-(N-Formyl-L-phenylalanyl)-6-deoxy-6-aminocyclomaltoheptaose (f-L-Phe-β-CD) is one of CD derivatives with excellent ability of chiral recognition. In order to make clear the mechanism of chiral recognition, the conformation of free f-L-Phe-β-CD has been studied by using 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. From the measurement of 1H homonuclear Overhauser enhancement on the rotating frame, it is concluded that f-L-Phe-residue of the f-L-Phe-β-CD is inserted into its cavity from the upside of primary hydroxyl groups of the macrocyclic ring. Analysis of 1H and 13C spectra of f-L-Phe-β-CD and model compounds of f-L-Phe-residue also support this conclusion. The macrocyclic ring is found to be distorted. © 1990 The Chemical Society of Japan.