Addition of maltodextrins to the nonreducing-end of acarbose by reaction of acarbose with cyclomaltohexaose and cyclomaltodextrin glucanyltransferase. 2002

Seung-Heon Yoon, and John F Robyt
Laboratory of Carbohydrate Chemistry and Enzymology, Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University, Ames, IA 50011, USA.

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.

UI MeSH Term Description Entries
D008320 Maltose A dextrodisaccharide from malt and starch. It is used as a sweetening agent and fermentable intermediate in brewing. (Grant & Hackh's Chemical Dictionary, 5th ed)
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D002855 Chromatography, Thin Layer Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D003505 Cyclodextrins A homologous group of cyclic GLUCANS consisting of alpha-1,4 bound glucose units obtained by the action of cyclodextrin glucanotransferase on starch or similar substrates. The enzyme is produced by certain species of Bacillus. Cyclodextrins form inclusion complexes with a wide variety of substances. Cycloamylose,Cyclodextrin,Cyclodextrin Derivatives,Cyclomaltooligosaccharides,Derivatives, Cyclodextrin
D003912 Dextrins A group of low-molecular-weight carbohydrates produced by the hydrolysis of STARCH or GLYCOGEN. They are mixtures of polymers of D-glucose units linked by alpha-(1->4) or alpha-(1->6) glycosidic bonds. Dextrin
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D005964 Glucosyltransferases Enzymes that catalyze the transfer of glucose from a nucleoside diphosphate glucose to an acceptor molecule which is frequently another carbohydrate. EC 2.4.1.-. Glucosyltransferase
D006031 Glycosylation The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION). Protein Glycosylation,Glycosylation, Protein
D001407 Bacillus A genus of BACILLACEAE that are spore-forming, rod-shaped cells. Most species are saprophytic soil forms with only a few species being pathogenic. Bacillus bacterium

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