Addition of maltodextrins to the nonreducing-end of acarbose by reaction of acarbose with cyclomaltohexaose and cyclomaltodextrin glucanyltransferase.
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.
Yoon
Seung-Heon
SH
Laboratory of Carbohydrate Chemistry and Enzymology, Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University, Ames, IA 50011, USA.
Robyt
John F
JF
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
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