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Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography
Author(s) -
Fu Dongmei,
Zhang Xue,
Zhang Hao,
Fu Qing,
Jin Yu,
Yan Jingyu,
Li Xianzhen
Publication year - 2021
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.202001193
Subject(s) - chemistry , chromatography , extraction (chemistry) , solid phase extraction , column chromatography , high performance liquid chromatography , particle size , hydrophilic interaction chromatography
A simple and efficient method was developed for the preparation of high‐purity trehalulose from the waste syrup of isomaltulose production. The waste syrup was pre‐treated with C18 solid‐phase extraction, where 98% decolorization and 97% reducing sugar recovery were obtained, followed by hydrophilic interaction liquid chromatography separation on a cysteine‐bonded zwitterionic column. Under optimized conditions, trehalulose was separated from isomaltulose isomer and prepared on a semi‐preparative scale with >99% purity. The structure of the prepared trehalulose was subsequently confirmed by nuclear magnetic resonance, and three tautomers of trehalulose ( α ‐D‐glucosylpyranosyl‐1,1‐ β ‐D‐fructopyranose, α ‐D‐glucosylpyranosyl‐1,1‐ β ‐D‐fructofuranose, and α ‐D‐glucosylpyranosyl‐1,1‐ α ‐D‐fructofuranose) were detected and completely characterized by 13 C NMR spectroscopy for the first time in this study. The tautomerization of α ‐D and β ‐D type transition was observed by hydrophilic interaction liquid chromatography on an AdvanceBio Glycan Mapping column, with smaller particle size (2.7 μm). Furthermore, the prepared trehalulose was applied as a standard for trehalulose quantification during the sucrose conversion by Klebsiella sp. LX3. The combination of solid‐phase extraction and hydrophilic interaction liquid chromatography offers a new avenue for the preparation of sugar isomers from complex natural or fermentation products.