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Structural analysis of novel kestose isomers isolated from sugar beet molasses

Author:
Shiomi, Norio, Abe, Tatsuya, Kikuchi, Hiroto, Aritsuka, Tsutomu, Takata, Yusuke, Fukushi, Eri, Fukushi, Yukiharu, Kawabata, Jun, Ueno, Keiji, Onodera, Shuichi
Source:
Carbohydrate research 2016 v.424 pp. 1-7
ISSN:
0008-6215
Subject:
gas chromatography-mass spectrometry, high performance liquid chromatography, isomers, kestose, molasses, nuclear magnetic resonance spectroscopy, sugar beet
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 1H and 13C 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.
Agid:
5287136