Structural analysis of novel kestose isomers isolated from sugar beet molasses

Abstract Eight kestose isomers were isolated from sugar beet molasses by carbon–Celite column chromatography and HPLC. GC–FID and GC–MS analyses of methyl derivatives, MALD-TOF-MS measurements and NMR spectra were used to confirm the structural characteristics of the isomers. The 1 H and 13 C NMR signals of each isomer saccharide were assigned using COSY, E-HSQC, HSQC–TOCSY, HMBC and H2BC techniques. These kestose isomers were identified as α-D-fructofuranosyl-(2- > 2)-α-D-glucopyranosyl-(1  2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2- > 3)-β-D-fructofuranosyl-(2  1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2- > 4)-β-D-fructofuranosyl-(2  1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 4)-β-D-fructofuranosyl-(2  1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 3)-α-D-glucopyranosyl-(1  2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2- > 1)-β-D-fructofuranosyl-(2  1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2- > 6)-α-D-glucopyranosyl-(1  2)-β-D-fructofuranoside, and α-D-fructofuranosyl-(2- > 6)-β-D-fructofuranosyl-(2  1)-α-D-glucopyranoside. The former five compounds are novel saccharides.