Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography

Abstract

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.

Hydrophilic, dual amino acid–functionalized zinc sulfide quantum dot for specific identification of N‐glycopeptides from biological samples

“…In recent years, several strategies have been developed for selective enrichment of glycopeptides, including hydrophilic interaction liquid chromatography (HILIC), 16 boric acid affinity chromatography (BAAC), 17 lectin affinity chromatography (LAC), 18 and hydrazine chemistry (HC) 19 . Among them, HILIC has developed significantly due to its simple operation process and unbiased enrichment of different N ‐glycopeptides 20,21 . A HILIC material is usually required to have excellent hydrophilicity and high specific surface area to increase the enrichment efficiency.…”

“…19 Among them, HILIC has developed significantly due to its simple operation process and unbiased enrichment of different Nglycopeptides. 20,21 A HILIC material is usually required to have excellent hydrophilicity and high specific surface area to increase the enrichment efficiency. At present, several hydrophilic nanomaterials based on different substrates have been successfully used for the enrichment of glycopeptides, such as silica nanoparticles, 22 graphene nanosheets, 23 metal-organic frameworks (MOFs).…”