title: Transfructosylation of thiol group by beta-fructofuranosidases.
abstract: Beta-fructofuranosidase fructosylated not only the hydroxyl group but also the thiol group of 2-mercaptoethanol in a transfer reaction using sucrose as a donor substrate. The enzymes from Candida utilis and Saccharomyces cerevisiae (bakers' yeast) were effective catalysts for the thio-fructofuranosylation. The thio-fructosylation product was isolated by activated carbon chromatography and its structure was confirmed by Fab-mass spectrometry and NMR spectroscopy. The thio-fructofuranoside was synthesized effectively at around 3.0 M for the acceptor concentration. The product increased with the sucrose concentration at least up to 1.9 M. O-Fructofuranoside was simultaneously synthesized at an early stage of the reaction, although it was hydrolyzed on further incubation. On the contrary, the thio-fructofuranoside accumulated efficiently after synthesis, indicating it was very stable against the hydrolytic action of the beta-fructofranosidase.
authors.affiliation: Osaka Municipal Technical Research Institute, Japan. nakanohi@city.osaka.jp
authors.forename: H
authors.initials: H
authors.lastname: Nakano
authors.forename: H
authors.initials: H
authors.lastname: Murakami
authors.forename: M
authors.initials: M
authors.lastname: Shizuma
authors.forename: T
authors.initials: T
authors.lastname: Kiso
authors.forename: T L
authors.initials: TL
authors.lastname: de Araujo
authors.forename: S
authors.initials: S
authors.lastname: Kitahata
mesh_terms: D002236:Carbohydrate Conformation; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000378:metabolism*; D008623:Mercaptoethanol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D013395:Sucrose / Q000378:metabolism; D043324:beta-Fructofuranosidase
chemical_list: D005632:Fructose; D013395:Sucrose; D008623:Mercaptoethanol; D006026:Glycoside Hydrolases; D043324:beta-Fructofuranosidase