Journal
CHEMSUSCHEM
Volume 12, Issue 4, Pages 848-857Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201802580
Keywords
amination; biocatalysis; carbohydrates; domino reactions; enzymes
Funding
- Academy of Finland [308996, 252183, 298250]
- European Research Council (ERC) Consolidator Grant [BHIVE-648925]
- German Research Foundation (DFG) [Bo1862/16-1]
- EU (Horizon2020) [722610]
- Academy of Finland (AKA) [308996, 252183, 298250, 308996, 298250, 252183] Funding Source: Academy of Finland (AKA)
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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 omega-transaminase from Chromobacterium violaceum (Cvi-omega-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-omega-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.
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