375372-11-5Relevant articles and documents
Transglycosylation reactions of Bacillus stearothermophilus maltogenic amylase with acarbose and various acceptors
Park, Kwan Hwa,Kim, Myo Jeong,Lee, Hee Seob,Han, Nam Soo,Kim, Doman,Robyt, John F.
, p. 235 - 246 (2007/10/03)
It was observed that Bacillus stearothermophilus maltogenic amylase cleaved the first glycosidic bond of acarbose to produce glucose and a pseudotrisaccharide (PTS) that was transferred to C-6 of the glucose to give an α-(1→6) glycosidic linkage and the formation of isoacarbose. The addition of a number of different carbohydrates to the digest gave transfer products in which PTS was primarily attached α-(1→6) to D-glucose, D-mannose, D-galactose, and methyl α-d-glucopyranoside. With d-fructopyranose and d-xylopyranose, PTS was linked α-(1→5) and α-(1→4), respectively. PTS was primarily transferred to C-6 of the nonreducing residue of maltose, cellobiose, lactose, and gentiobiose. Lesser amounts of α-(1→3) and/or α-(1→4) transfer products were also observed for these carbohydrate acceptors. The major transfer product to sucrose gave PTS linked α-(1→4) to the glucose residue. α,α-Trehalose gave two major products with PTS linked α-(1→6) and α-(1→4). Maltitol gave two major products with PTS linked α-(1→6) and α-(1→4) to the glucopyranose residue. Raffinose gave two major products with PTS linked α-(1→6) and α-(1→4) to the D-galactopyranose residue. Maltotriose gave two major products with PTS linked α-(1→6) and α-(1→4) to the nonreducing end glucopyranose residue. Xylitol gave PTS linked α-(1→5) as the major product and D-glucitol gave PTS linked α-(1→6) as the only product. The structures of the transfer products were determined using thin layer-chromatography, high-performance ion chromatography, enzyme hydrolysis, methylation analysis and 13C NMR spectroscopy. The best acceptor was gentiobiose, followed closely by maltose and cellobiose, and the weakest acceptor was D-glucitol. Copyright (C) 1998 Elsevier Science Ltd.
