Synthesis of acarbose analogues by transglycosylation reactions of Leuconostoc mesenteroides B-512FMC and B-742CB dextransucrases.
Two new acarbose analogues were synthesized by the reaction of acarbose with sucrose and dextransucrases from Leuconostoc mesenteroides B-512FMC and B-742CB. The major products for each reaction were subjected to yeast fermentation, and then separated and purified by Bio-Gel P2 gel permeation chromatography and descending paper chromatography. The structures of the products were determined by one- and two-dimensional 1H and 13C NMR spectroscopy and by matrix-assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF MS). B-512FMC-dextransucrase produced one major acarbose product, 2(I)-alpha-D-glucopyranosylacarbose and B-742CB-dextransucrase produced two major acarbose products, 2(I)-alpha-D-glucopyranosylacarbose and 3(IV)-alpha-D-glucopyranosylacarbose.
Yoon
Seung-Heon
SH
Laboratory of Carbohydrate Chemistry and Enzymology, 4252 Molecular Biology BLDG, Iowa State University, Ames 50011, USA.
Robyt
John F
JF
D020909:Acarbose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D002845:Chromatography; D005285:Fermentation; D005964:Glucosyltransferases / Q000378:metabolism*; D006031:Glycosylation; D007934:Leuconostoc / Q000201:enzymology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013395:Sucrose / Q000737:chemistry
D013395:Sucrose; D005964:Glucosyltransferases; C020025:dextransucrase; D020909:Acarbose