Carbohydrate Research 2000-07-24

Determination of the substituent distribution in O-sulfonylbutyl-(1-->4)-glucans.

N Rogmann, P Jones, P Mischnick

Index: Carbohydr. Res. 327(3) , 275-85, (2000)

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Abstract

A method has been developed to determine the distribution of substituents in the glucose units of sulfonylbutylethers of cyclomaltoheptaose (beta-cyclodextrin). This method involves hydrolysis of the glucosidic linkages, permethylation, formation of sulfonylchlorides and subsequent transformation to the permethylated sulfonylfluoride derivatives. The latter were thermostable and could be analyzed by GLC and identified by EI and CIMS. For confirmation, the 2-, 3-, and 6-O-substituted standard compounds were independently synthesized and characterized by NMR and GLC-MS.