Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and Leuconostoc mesenteroides B-742CB dextransucrase

摘要

beta-Salicin is a naturally occurring glycoside found in the bark of poplar and willow trees.Ancient man used it as an analgesic and antipyretic.It has a D-glucopyranose unit attached by a beta-linkage to the phenolic hydroxyl of salicyl alcohol.Two new salicin analogues have been enzymatically synthesized by transglycosylation reactions:(a)by the reaction of Bacillus macerans cyclomaltodextrin glucanyltransferase with cyclomaltohexaose and salicyl alcohol,followed by reactions with alpha amylase and glucoamylase to give D-glucopyranose attached by an ex-linkage to the phenolic hydroxyl of salicyl alcohol as the major product,alpha-salicin;and(b)by the reaction of Leuconostoc mesenteroides B-742CB dextransucrase with sucrose and salicyl alcohol,followed by reactions with dextranase and glucoamylase to give alpha-D-glucopyranose attached to the primary alcohol hydroxyl of salicyl alcohol as the major product,alpha-isosalicin.