Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades

Ville Aumala, Filip Mollerup, Edita Jurak, Fabian Blume, Johanna Karppi, Antti E. Koistinen, Eva Schuiten, Moritz Voß, Uwe Bornscheuer, Jan Deska, Emma R. Master*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)
155 Downloads (Pure)

Abstract

Plant-derived carbohydrates are an abundant renewable resource. Transformation of carbohydrates into new products, including amine-functionalized building blocks for biomaterials applications, can lower reliance on fossil resources. Herein, biocatalytic production routes to amino carbohydrates, including oligosaccharides, are demonstrated. In each case, two-step biocatalysis was performed to functionalize d-galactose-containing carbohydrates by employing the galactose oxidase from Fusarium graminearum or a pyranose dehydrogenase from Agaricus bisporus followed by the ω-transaminase from Chromobacterium violaceum (Cvi-ω-TA). Formation of 6-amino-6-deoxy-d-galactose, 2-amino-2-deoxy-d-galactose, and 2-amino-2-deoxy-6-aldo-d-galactose was confirmed by mass spectrometry. The activity of Cvi-ω-TA was highest towards 6-aldo-d-galactose, for which the highest yield of 6-amino-6-deoxy-d-galactose (67 %) was achieved in reactions permitting simultaneous oxidation of d-galactose and transamination of the resulting 6-aldo-d-galactose.

Original languageEnglish
JournalChemSusChem
DOIs
Publication statusPublished - 1 Jan 2019
MoE publication typeA1 Journal article-refereed

Keywords

  • amination
  • biocatalysis
  • carbohydrates
  • domino reactions
  • enzymes

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  • Projects

    Capturing Oxidoreductases for Carbohydrate Oligomer Activation

    Karppi, J., Master, E. & Mollerup, F.

    01/09/201731/12/2020

    Project: Academy of Finland: Other research funding

    Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations

    Blume, F., Jäger, C., Deska, J., Naapuri, J., Liu, Y. & Kiefer, A.

    01/09/201631/08/2021

    Project: Academy of Finland: Other research funding

    BHIVE: Bio-derived HIgh Value polymers through novel Enzyme function

    Mollerup, F., Karppi, J., Jurak, E., Aumala, V., Master, E., Monschein, M. & Leamon, A. K. M. A. A.

    01/09/201531/10/2020

    Project: EU: ERC grants

    Equipment

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