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 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.
Original language | English |
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Pages (from-to) | 848-857 |
Number of pages | 10 |
Journal | Chemsuschem |
Volume | 12 |
Issue number | 4 |
DOIs | |
Publication status | Published - 21-Feb-2019 |
Keywords
- amination
- biocatalysis
- carbohydrates
- domino reactions
- enzymes
- TEMPO-MEDIATED OXIDATION
- GALACTOSE-OXIDASE
- CHEMOENZYMATIC SYNTHESIS
- PYRANOSE DEHYDROGENASE
- ALCOHOL-DEHYDROGENASE
- ASYMMETRIC-SYNTHESIS
- OMEGA-TRANSAMINASE
- STRUCTURAL BASIS
- BUILDING-BLOCKS
- BINDING MODULE