Synthesis, structural analysis and application of novel acarbose-fructoside using levansucrase |
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| Authors: | Seung-Hee Nam Young-Hwan Moon Jin Kang Young-Min Kim John F Robyt Doman Kim |
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| Institution: | aJeonnam Agricultural Research & Extension Services, Jeonnam 520-715, Republic of Korea;bDepartment of Cell Biology and Molecular Genetics, University of Maryland, College Park, MD 20742, USA;cSchool of Biological Sciences and Technology and Research Institute for Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea;dDepartment of Biochemistry, Biophysics and Molecular Biology, Iowa State University, Ames, IA 50011, USA |
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| Abstract: | Acarbose-fructoside (acarbose-Fru) was newly synthesized via the acceptor reaction of a levansucrase from Leuconostoc mesenteroides B-512 FMC with acarbose and sucrose. The resultant product was separated with 10.5% purification yield via Bio-gel P-2 column chromatography and HPLC. Its structure was determined to be 1I-β-d-fructofuranosyl α-acarbose, according to the results of 1H, 13C, HSQC, and HMBC analyses. Acarbose-Fru was inhibited competitively on α-glucosidase (A. niger and baker's yeast) but mixed noncompetitively on α-amylases (A. oryzae and porcine pancreatic). Compared to acarbose, acarbose-Fru exhibited inhibition potency of 1.12 or 1.52 on A. niger α-glucosidase or A. oryzae α-amylase, respectively. Additionally, acarbose-Fru was identified as a novel substrate for dextransucrase with Km and Vmax values of 189.0 mM and 8.51 μmol/(mg min), respectively. Therefore, acarbose-Fru as a substrate might be synthesized novel acarbose derivatives by using dextransucrase. |
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| Keywords: | Acarbose Acceptor reaction Levansucrase Leuconostoc mesenteroides Dextransucrase |
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