Cyclodextrin-Dialdehyde Prepared by Periodate Oxidation

Abstract

Dialdehyde derivative of cyclodextrin (dial-CD) was prepared by oxidation with sodium metaperiodate, because the oxidative cleavage with periodate would theoretically provide 2′, 3′-dialdehyde derivatives of the α-1, 4-linked glucans. The α-CD oxidized with equimolar periodate (dial-α-CD I) was separated from the unoxidized native α-CD by column chromatography on Sephadex G-15, where the peak of dial-α-CD I was eluted faster than the native α-CD and corresponded to the reducing power. Since the hydrated forms of dial-CD gave no characteristic spectral pattern of the dialdehyde groups, the structure of the dial-CD was deduced by IR and 13C-NMR spectral analysis for a dicarboxylate derivative of the dial-α-CD. The dial-α-CD I has an average of 3.5 glucose residues oxidized into the dialdehyde structure. Among the possible 13 isomers of the dial:α-CD, isomers IA, IIAB, IIAC, IIIABC, and IIIABD were the predominant forms, which were identified by the measurement of maltooligosaccharides derived from the dial-α-CD I by NaBH4 reduction and acid treatment. Moreover, the reactivity of the dial-α-CD I was demonstrated by adduct formation with lysine and glycine, which was analyzed by gel filtration patterns on a Sephadex G-15 column. © 1988, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.