Synthesis of Novel Heterobranched β-Cyclodextrins from α-D-Mannosyl Maltotriose and β-Cyclodextrin by the Reverse Action of Pullulanase, and Isolation and Characterization of the Products

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α-D-Mannosyl-maltotriose (Man-G3) were synthesized from methyl α-mannoside and maltotriose by the transfer action of α-mannosidase. (Man-G3)-βCD and (Man-G3)_2-βCD were produced in about 20% and 4% yield, respectively when Aerobacter aerogenes pullulanase (160 units per 1 g of Man-G3) was incubated with the mixture of 1.6M Man-G3 and 0.16M βCD at 50℃ for 4 days. The reaction products, (Man-G3)-βCD were separated to three peaks by HPLC analysis on a YMC-PACK A-323-3 column and (Man-G3)_2-βCD were separated to several peaks by HPLC analysis on a Daisopak ODS column. The major product of (Man-G3)-βCDs was identified as 6-O-α-(6^3-O-α-D-mannosyl-maltotriosyl)-βCD by FAB-MS and NMR spectroscopies. The structures of (Man-G3)_2-βCDs were analyzed by TOF-MS and NMR spectroscopies, and confirmed by comparison of elution profiles of their hydrolyzates by α-mannosidase and glucoamylase on a graphitized carbon column with those of the authentic di-glucosyl-βCDs. The structures of three main components of (Man-G3)_2-βCDs were identified as 6^1,6^2-, 6^1,6^3-and 6^1,6^4-di-O-(6^3-O-α-D-mannosyl-maltotriosyl)-βCD.
社団法人日本農芸化学会の論文
2000-11-23