Abstract
Two sets of diastereomers, mono[6-deoxy-6-(L- and D-tyrosylamino)]-β-cyclodextrin (1, 2) and mono[6-deoxy-6N(N′-formyl L- and D-phenylglycylamino)]-β-cyclodextrin (3, 4), were prepared. Based on NMR and fluorescence spectroscopic studies, it was suggested that the aromatic group attached to 1, 2, 3, and 4 was located at the outside of the cavity and that these CDs had an expanded and distorted cavity enclosed by the aromatic group and the parent CD wall. The conformation of 1 and 2 is “capped type,” whereas that of 3 and 4 is “pendant.” The difference between 3 and 4, which is only one chiral carbon at the appended group among 36 chiral carbons comprising these total modified CDs, induced more remarkable differences than that among the “capped type” CD in (1) the conformation or hydrophobic cavity shape, (2) selectivity for guest molecules, and (3) “induced-fit” behavior. These differences seem to be caused by a combination of weak interactions. The difference between 3 and 4 having a formyl group at the middle of the arm is observed in the phenyl ring and the “fiexible arm” environment, whereas that between 1 and 2 having a hydroxyl group as the hydrogen bonding point at the head of the appended group is observed in the macrocyclic ring.
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Takahashi, K., Furushoh, R. Diastereomeric Differences of “Pendant Type” Monosubstituted Cyclodextrins, Mono-[6-deoxy-6N(N′-formyl L- and D-phenylglycylamino)]-β-cyclodextrin in Conformation and “Induced-fit” Behavior. Polym J 28, 458–464 (1996). https://doi.org/10.1295/polymj.28.458
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DOI: https://doi.org/10.1295/polymj.28.458
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