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Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades
Author(s) -
Aumala Ville,
Mollerup Filip,
Jurak Edita,
Blume Fabian,
Karppi Johanna,
Koistinen Antti E.,
Schuiten Eva,
Voß Moritz,
Bornscheuer Uwe,
Deska Jan,
Master Emma R.
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802580
Subject(s) - galactose , chemistry , transamination , biochemistry , biocatalysis , galactose oxidase , transaminase , oxidoreductase , monosaccharide , organic chemistry , amino acid , enzyme , catalysis , ionic liquid
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.