Enzymatic synthesis of acarbose oligosaccharide analogues as new enzyme inhibitors

Acarbose, a pseudotetrasaccharide and inhibitor for several carbohydrases, was modified at the reducing-end by Bacillus stearothermophilus maltogenic amylase transglycosylation reactions with several mono- and disaccharide acceptors to give new, specific, and more potent carbohydrase inhibitors. Acarbose was also modified at the nonreducing-end by B. macerans cyclomaltodextrin glucanyltransferase transglycosylation reactions between cyclomaltohexaose and acarbose. These analogues have been found to be very potent and specific inhibitors for porcine pancreatic, Aspergillus oryzae, and Bacillus amyloliquefaciens, alpha-amylases with K-I values of 10, 30, and 40 nM respectively.