title: Addition of maltodextrins to the nonreducing-end of acarbose by reaction of acarbose with cyclomaltohexaose and cyclomaltodextrin glucanyltransferase.
abstract: 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 alpha- to the C-4-OH group of the nonreducing-end cyclohexene ring of acarbose, indicating that the maltodextrins were attached alpha-(1-->4) to the nonreducing-end cyclohexene of acarbose.
authors.affiliation: Laboratory of Carbohydrate Chemistry and Enzymology, Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University, Ames, IA 50011, USA.
authors.forename: Seung-Heon
authors.initials: SH
authors.lastname: Yoon
authors.forename: John F
authors.initials: JF
authors.lastname: Robyt
mesh_terms: D020909:Acarbose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000302:isolation & purification; D001407:Bacillus / Q000201:enzymology; D001426:Bacterial Proteins / Q000737:chemistry; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer / Q000379:methods; D003505:Cyclodextrins / Q000737:chemistry* / Q000302:isolation & purification; D003912:Dextrins / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D005964:Glucosyltransferases / Q000737:chemistry*; D006031:Glycosylation; D008320:Maltose / Q000737:chemistry*; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D047391:alpha-Cyclodextrins
chemical_list: D001426:Bacterial Proteins; D003505:Cyclodextrins; D003912:Dextrins; D004791:Enzyme Inhibitors; D047391:alpha-Cyclodextrins; D008320:Maltose; C049580:dextrin maltose; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D020909:Acarbose; C032613:alpha-cyclodextrin