Addition of maltodextrins to the nonreducing-end of acarbose by reaction of acarbose with cyclomaltohexaose and cyclomaltodextrin glucanyltransferase

• Published in: Carbohydrate research Vol. 337; no. 6; pp. 509 - 516
• Main Authors: Yoon, Seung-Heon, Robyt, John F
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.03.2002; Elsevier
• Subjects: 13C NMR spectroscopy; Acarbose - analogs & derivatives; Acarbose - chemical synthesis; Acarbose - isolation & purification; Acarbose analogues; alpha-Cyclodextrins; Bacillus - enzymology; Bacterial Proteins - chemistry; Biochemistry & Molecular Biology; Carbohydrate Sequence; Chemistry; Chemistry, Applied; Chemistry, Organic; Chromatography, Thin Layer - methods; Cyclodextrins - chemistry; Cyclodextrins - isolation & purification; Cyclomaltodextrin glucanyltransferase; Cyclomaltohexaose; Dextrins - chemistry; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Glucosyltransferases - chemistry; Glycosylation; Life Sciences & Biomedicine; Maltododecaose; Maltohexaose; Maltooctadecaose; Maltose - chemistry; Molecular Sequence Data; Nuclear Magnetic Resonance, Biomolecular - methods; Physical Sciences; Science & Technology; Transglycosylation reactions; Acarbose analogues; Transglycosylation reactions; Cyclomaltodextrin glucanyltransferase; 13C NMR spectroscopy; Maltohexaose; Maltododecaose; Maltooctadecaose; Cyclomaltohexaose; maltododecaose; acarbose analogues; ALPHA-GLUCOSIDASE; cyclomaltohexaose; maltooctadecaose; GLUCOAMYLASE; INHIBITION; transglycosylation reactions; C-13 NMR spectroscopy; AMYLASE; PURIFICATION; cyclomaltodextrin glucanyltransferase; maltohexaose
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(02)00018-6

New kinds of acarbose analogues were synthesized by the reaction of acarbose with cyclomaltohexaose and cyclomaltodextrin glucanyltransferase (CGTase). Three major CGTase coupling products were separated and purified by Bio-Gel P2 gel-permeation chromatography. Digestion of the three products by beta-amylase and glucoamylase showed that they were composed of maltohexaose (G6), maltododecaose (G12), and maltooctadecaose (G18), respectively, attached to the nonreducing-end of acarbose. 13C NMR of the glucoamylase product ( d-glucopyranosyl-acarbose) showed that the d-glucose moiety was attached α- to the C-4-OH group of the nonreducing-end cyclohexene ring of acarbose, indicating that the maltodextrins were attached α-(1→4) to the nonreducing-end cyclohexene of acarbose. Graphic