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Applied Biochemistry and Biotechnology

, Volume 186, Issue 3, pp 681–691 | Cite as

Synthesis of a Fucosylated Trisaccharide Via Transglycosylation by α-l-Fucosidase from Thermotoga maritima

  • Francisco Guzmán-Rodríguez
  • Sergio Alatorre-Santamaría
  • Lorena Gómez-Ruiz
  • Gabriela Rodríguez-Serrano
  • Mariano García-Garibay
  • Alma Cruz-Guerrero
Article

Abstract

Fucosylated oligosaccharides, such as 2′-fucosyllactose in human milk, have important biological functions such as prebiotics and preventing infection. In this work, the effect of an acceptor substrate (lactose) and the donor substrate 4-nitrophenyl-α-l-fucopyranoside (pNP-Fuc) on the synthesis of a fucosylated trisaccharide was studied in a transglycosylation reaction using α-l-fucosidase from Thermotoga maritima. Conducting a matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), it was demonstrated that synthesized oligosaccharide corresponded to a fucosylated trisaccharide, and high-performance liquid chromatography (HPLC) of the hydrolyzed compound confirmed it was fucosyllactose. As the concentration of the acceptor substrate increased, the concentration and synthesis rate of the fucosylated trisaccharide also increased, and the highest concentration obtained was 0.883 mM (25.2% yield) when using the higher initial lactose concentration (584 mM). Furthermore, the lower donor/acceptor ratio had the highest synthesis, so at the molar ratio of 0.001, a concentration of 0.286 mM was obtained (32.5% yield).

Keywords

Fucosyllactose Transglycosylation Fucosidase Thermotoga maritima 

Notes

Funding information

This work was supported by Consejo Nacional de Ciencia y Tecnología (financial support number 50370).

Compliance with Ethical Standards

Conflict of Interest

The authors declare that they have no conflict of interest.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Departamento de BiotecnologíaUniversidad Autónoma Metropolitana-IztapalapaMexico CityMexico
  2. 2.Departamento de Ciencias de la Alimentación, División de Ciencias Biológicas y de la SaludUniversidad Autónoma MetropolitanaLerma de VilladaMexico

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