Glycoconjugate Journal

, Volume 35, Issue 1, pp 31–40 | Cite as

Enzymatic synthesis of fucose-containing galacto-oligosaccharides using β-galactosidase and identification of novel disaccharide structures

  • Anne Usvalampi
  • Hannu Maaheimo
  • Olli Tossavainen
  • Alexander D. Frey
Original Article


Fucosylated oligosaccharides have an important role in maintaining a healthy immune system and homeostatic gut microflora. This study employed a commercial β-galactosidase in the production of fucose-containing galacto-oligosaccharides (fGOS) from lactose and fucose. The production was optimized using experiment design and optimal conditions for a batch production in 3-liter scale. The reaction product was analyzed and the produced galactose-fucose disaccharides were purified. The structures of these disaccharides were determined using NMR and it was verified that one major product with the structure Galβ1–3Fuc and two minor products with the structures Galβ1–4Fuc and Galβ1–2Fuc were formed. Additionally, the product composition was defined in more detail using several different analytical methods. It was concluded that the final product contained 42% total monosaccharides, 40% disaccharides and 18% of larger oligosaccharides. 290 μmol of fGOS was produced per gram of reaction mixture and 37% of the added fucose was bound to fGOS. The fraction of fGOS from total oligosaccharides was determined as 44%. This fGOS product could be used as a new putative route to deliver fucose to the intestine.


β-galactosidase Transglycosylation Fucose Hetero-oligosaccharide Galacto-oligosaccharide 


Compliance with ethical standards

Conflicts of interest

The authors declare that they have no conflicts of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

10719_2017_9794_MOESM1_ESM.pdf (387 kb)
ESM 1 (PDF 386 kb)


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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Department of Bioproducts and BiosystemsAalto University School of Chemical EngineeringEspooFinland
  2. 2.Technical Research Center of FinlandEspooFinland
  3. 3.Valio Ltd.HelsinkiFinland

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