Preparation of 2,3,6,2′,3′,4′,6′-hepta- O-acetyl-maltose/cellobiose by enzymatic hydrolysis of maltose/cellobiose octaacetate

• Published in: Carbohydrate research 1994-12, Vol.265 (2), p.311-318
• Main Authors: Ong, Geok-Toh, Chang, Kung-Yao, Wu, Shih-Hsiung, Wang, Kung-Tsung
• Format: Article
• Language: English
• Subjects: Alcalase deacetylation; Anomeric O-deacetylation; Carbohydrate Conformation; Carbohydrate Sequence; Cellobiose - analogs & derivatives; Cellobiose - chemical synthesis; Cellobiose - chemistry; Cellobiose hepta-acetate; Endopeptidases; Enzymatic deacetylation; Hydrolysis; Indicators and Reagents; Lipase; Lipase deacetylation; Maltose - analogs & derivatives; Maltose hepta-acetate; Molecular Sequence Data; Protease deacetylation
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/0008-6215(94)00237-1

Maltose and cellobiose octaacetates were hydrolyzed by various hydrolytic enzymes exclusively at the anomeric position. More than ten enzymes were examined for the hydrolysis and all were found to preferentially cleave the anomeric esters. The products obtained from the hydrolysis of maltose octaacetate by various enzymes showed two peaks in high performance liquid chromatography. After nuclear magnetic resonance analysis, two products were identified as the alpha and beta forms of 2,3,6,2',3',4',6' -hepta-O-acetyl-maltose that interconverted through mutarotation. Two products were also obtained from the hydrolysis of cellobiose octaacetate. The structures of the products were elucidated and the chemical shifts were established.