title: Di-D-fructose dianhydrides and related oligomers from thermal treatments of inulin and sucrose.
abstract: Thermal treatment of anhydrous, acidified sucrose or inulin yields caramels containing monosaccharides and oligomers, predominantly dianhydrides and higher oligomers derived by the addition of glycosyl residues to dianhydrides. Fourteen dianhydrides, most of which comprise two fructose moieties, have been identified by mass spectroscopy of the per-O-trimethylsilyl ethers. Thirteen of these dianhydrides have been isolated and characterized; five of the dianhydrides are novel compounds and one of these is a glucose-fructose dianhydride. The dianhydrides and related oligomers are thought to have a prebiotic effect by stimulating the proliferation of bifidobacteria in the large intestine.
authors.affiliation: Shafizadeh Center for Wood and Carbohydrate Chemistry, University of Montana, Missoula 59812, USA.
authors.forename: M
authors.initials: M
authors.lastname: Manley-Harris
authors.forename: G N
authors.initials: GN
authors.lastname: Richards
mesh_terms: D000080:Acetals / Q000737:chemistry* / Q000302:isolation & purification; D000812:Anhydrides; D002240:Carbohydrate Sequence; D004146:Dioxanes / Q000737:chemistry* / Q000302:isolation & purification; D004187:Disaccharides / Q000737:chemistry* / Q000302:isolation & purification; D005632:Fructose; D006358:Hot Temperature; D007328:Insulin / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D009904:Optical Rotation; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013395:Sucrose / Q000737:chemistry*
chemical_list: D000080:Acetals; D000812:Anhydrides; D004146:Dioxanes; D004187:Disaccharides; D007328:Insulin; D009844:Oligosaccharides; D005632:Fructose; D013395:Sucrose