ArticleBiotechnology and bioengineering2020
Glycosynthase reaction meets the flow: Continuous synthesis of lacto-N-triose II by engineered β-hexosaminidase immobilized on solid support.
Article in Biotechnology and bioengineering, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 42 citations in OpenAlex.
- Catalytic Efficiency for the Chemoenzymatic Synthesis of Core Human Milk Oligosaccharides and Analogs via Sugar Oxazolines.Journal of agricultural and food chemistry · 2026Article
- Glycan synthesis with SpyCatcher-SpyTag immobilized Leloir-glycosyltransferases.Applied microbiology and biotechnology · 2025Article
- The P134Q Sucrose Phosphorylase: Subtle Changes in the Catalytic Properties Benefit the Production of 2-O-α-Glucosyl Glycerol.Biotechnology and bioengineering · 2025Article
- Glycosyltransferases: glycoengineers in human milk oligosaccharide synthesis and manufacturing.Frontiers in molecular biosciences · 2025Review
- Carbohydrate-active enzymes (CAZymes) in the gut microbiome.Nature reviews. Microbiology · 2022Review
- Substrate and Process Engineering for Biocatalytic Synthesis and Facile Purification of Human Milk Oligosaccharides.ChemSusChem · 2022Article
- Cell-Free Multi-Enzyme Synthesis and Purification of Uridine Diphosphate Galactose.Chembiochem : a European journal of chemical biology · 2022Article
- Biocatalysis in Continuous-Flow Microfluidic Reactors.Advances in biochemical engineering/biotechnology · 2022Article
- Recent advances in enzymatic synthesis of β-glucan and cellulose.Carbohydrate research · 2021Review
- Transglycosylation Activity of EngineeredInternational journal of molecular sciences · 2021Article
- Biocatalysis: Enzymatic Synthesis for Industrial Applications.Angewandte Chemie (International ed. in English) · 2021Review
- Enzymatic Synthesis of Glycans and Glycoconjugates.Advances in biochemical engineering/biotechnology · 2021Review
- Glycosynthase reaction meets the flow: Continuous synthesis of lacto-N-triose II by engineered β-hexosaminidase immobilized on solid support.Biotechnology and bioengineering · 2020Article
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Authors and funding
3 authors at 2 institutions in 2 countries.
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No grant is acknowledged in the PubMed record.
Abstract
The D746E variant of Bifidobacterium bifidum β-N-acetyl-hexosaminidase is a promising glycosynthase (engineered glycosidase deficient in hydrolase activity) for the synthesis of lacto-N-triose II (LNT II), a core structural unit of human milk oligosaccharides. Here, we develop a flow process for the glycosynthase reaction, which is the regioselective β-1,3-glycosylation of lactose from a d-glucosamine 1,2-oxazoline donor. Using the glycosynthase immobilized on agarose beads (∼30 mg/g) packed into a fixed bed (1 ml), we show stable continuous production of LNT II (145-200 mM) at quantitative yield from the donor substrate. The wild-type β-N-acetyl-hexosaminidase used under exactly comparable conditions gives primarily (∼85%) the hydrolysis product d-glucosamine. By enabling short residence times (2 min) that are challenging for mixed-vessel types of reactor to establish, the glycosynthase flow reactor succeeds in an effective uncoupling of the LNT II formation (∼80-100 mM/min) from the slower side reactions (decomposition of donor substrate, enzymatic hydrolysis of LNT II) to obtain optimum synthetic efficiency. Our study thus provides a strong case for the application of flow chemistry principles to glycosynthase reactions and by that, it reveals the important synergy between enzyme and reaction engineering for biocatalytic synthesis of oligosaccharides.
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