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1H NMR Study of Conformation of Formyl- l -phenylalanyl-6-deoxy-6-amino-cyclomaltoheptaose That Has Excellent Ability of Chiral Recognition

1990; Oxford University Press; Volume: 63; Issue: 11 Linguagem: Inglês

10.1246/bcsj.63.3175

1348-0634

Wataru Saka, Yasuhiko Yamamoto, Yoshio Inoue, Riichirǒ Chûjô, Keiko Takahashi, Kenjiro Hattori,

Carbohydrate Chemistry and Synthesis

Abstract 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.