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, 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

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5920-5924
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	24
Early online date	30 May 2019
DOIs	https://doi.org/10.1039/c9ob01089k
Publication status	First published - 30 May 2019
Externally published	Yes

Keywords

Amino Sugars/biosynthesis
Biocatalysis
Galactosyltransferases/chemistry
Lactose/chemistry
Molecular Structure
Recombinant Proteins/chemistry

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Huang, K., Parmeggiani, F., Ledru, H., Hollingsworth, K., Mas Pons, J., Marchesi, A., Both, P., Mattey, A. P., Pallister, E., Bulmer, G. S., van Munster, J. M., Turnbull, W. B., Galan, M. C., & Flitsch, S. L. (2019). Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases. Organic and Biomolecular Chemistry, 17(24), 5920-5924. Advance online publication. https://doi.org/10.1039/c9ob01089k

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

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.",

keywords = "Amino Sugars/biosynthesis, Biocatalysis, Galactosyltransferases/chemistry, Lactose/chemistry, Molecular Structure, Recombinant Proteins/chemistry",

author = "Kun Huang and Fabio Parmeggiani and Helene Ledru and Kristian Hollingsworth and {Mas Pons}, Jordi and Andrea Marchesi and Peter Both and Mattey, {Ashley P} and Edward Pallister and Bulmer, {Gregory S} and {van Munster}, {Jolanda M} and Turnbull, {W Bruce} and Galan, {M Carmen} and Flitsch, {Sabine L}",

year = "2019",

month = may,

day = "30",

doi = "10.1039/c9ob01089k",

language = "English",

volume = "17",

pages = "5920--5924",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "24",

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Huang, K, Parmeggiani, F, Ledru, H, Hollingsworth, K, Mas Pons, J, Marchesi, A, Both, P, Mattey, AP, Pallister, E, Bulmer, GS, van Munster, JM, Turnbull, WB, Galan, MC & Flitsch, SL 2019, 'Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases', Organic and Biomolecular Chemistry, vol. 17, no. 24, pp. 5920-5924. https://doi.org/10.1039/c9ob01089k

TY - JOUR

T1 - Enzymatic synthesis of N-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases

AU - Huang, Kun

AU - Parmeggiani, Fabio

AU - Ledru, Helene

AU - Hollingsworth, Kristian

AU - Mas Pons, Jordi

AU - Marchesi, Andrea

AU - Both, Peter

AU - Mattey, Ashley P

AU - Pallister, Edward

AU - Bulmer, Gregory S

AU - van Munster, Jolanda M

AU - Turnbull, W Bruce

AU - Galan, M Carmen

AU - Flitsch, Sabine L

PY - 2019/5/30

Y1 - 2019/5/30

N2 - 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.

AB - 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.

KW - Amino Sugars/biosynthesis

KW - Biocatalysis

KW - Galactosyltransferases/chemistry

KW - Lactose/chemistry

KW - Molecular Structure

KW - Recombinant Proteins/chemistry

U2 - 10.1039/c9ob01089k

DO - 10.1039/c9ob01089k

M3 - Article

C2 - 31165848

SN - 1477-0520

VL - 17

SP - 5920

EP - 5924

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

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

Abstract

Keywords

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