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

8 Citations (Scopus)
202 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
Pages (from-to)848-857
Number of pages10
JournalChemSusChem
Volume12
Issue number4
DOIs
Publication statusPublished - 21 Feb 2019
MoE publication typeA1 Journal article-refereed

Keywords

  • amination
  • biocatalysis
  • carbohydrates
  • domino reactions
  • enzymes

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