Enzymatic synthesis of a new derivative of thiamin, O-alpha-glucosylthiamin.
A new transglucosylated derivative of thiamin could be synthesized by the actions of cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus and glucoamylase from Rhizopus sp., in this order, on a mixture of dextrin and thiamin. The derivative was isolated in crystalline form and identified as 5'-O-(alpha-D-glucopyranosyl)thiamin by spectroscopy (FAB-MS, UV, 1H-NMR, and 13C-NMR), thiochrome formation with K3 [Fe(CN)6]-NaOH reagent, and the hydrolysis products by alpha- and beta-glucosidases. O-alpha-Glucosylthiamin was odorless and mildly sweet with no tongue-pricking taste, and was more stable than thiamin hydrochloride in aqueous solutions at pHs 7.0 and 9.3.
Uchida
K
K
Research Institute for Bioresources, Okayama University, Japan.
Suzuki
Y
Y
D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D002854:Chromatography, Paper; D003912:Dextrins / Q000737:chemistry; D001411:Geobacillus stearothermophilus / Q000201:enzymology* / Q000378:metabolism; D005087:Glucan 1,4-alpha-Glucosidase / Q000378:metabolism*; D005964:Glucosyltransferases / Q000378:metabolism*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D011522:Protons; D012233:Rhizopus / Q000201:enzymology* / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D013831:Thiamine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification
D002250:Carbon Radioisotopes; D003912:Dextrins; C107140:O-glucosylthiamine; D011522:Protons; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D005087:Glucan 1,4-alpha-Glucosidase; D013831:Thiamine