Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases

Kun Huang; Fabio Parmeggiani; Helene Ledru; Kristian Hollingsworth; Jordi Mas Pons; Andrea Marchesi; Peter Both; Ashley P. Mattey; Edward Pallister; Gregory S. Bulmer; Jolanda M. van Munster; W. Bruce Turnbull; M. Carmen Galan; Sabine L. Flitsch

doi:10.1039/C9OB01089K

Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases†

Kun Huang,

^a Fabio Parmeggiani,

^a Helene Ledru,^b Kristian Hollingsworth,^c Jordi Mas Pons,^b Andrea Marchesi,

^a Peter Both,^a Ashley P. Mattey,^a Edward Pallister,^a Gregory S. Bulmer,^a Jolanda M. van Munster,^a W. Bruce Turnbull,

^c M. Carmen Galan

*^b and Sabine L. Flitsch

*^a

Author affiliations

* Corresponding authors

^a Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, Manchester, UK
E-mail: sabine.flitsch@manchester.ac.uk

^b School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK
E-mail: m.c.galan@bristol.ac.uk

^c School of Chemistry and Asbury Centre for Structural Molecular Biology, The University of Leeds, Woodhouse Lane, Leeds, UK

Abstract

Utilising a fast and sensitive screening method based on imidazolium-tagged probes, we report unprecedented reversible activity of bacterial β1,4-galactosyltransferases to catalyse the transgalactosylation from lactose to N-acetylglucosamine to form N-acetyllactosamine in the presence of UDP. The process is demonstrated by the preparative scale synthesis of pNP-β-LacNAc from lactose using β1,4-galactosyltransferase NmLgtB-B as the only biocatalyst.

This article is part of the themed collections: Chemical Biology in OBC and Celebrating our 2020 Prize and Award winners

Organic & Biomolecular Chemistry

Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases†

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Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases

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