Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades

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Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades. / Aumala, Ville; Mollerup, Filip; Jurak, Edita; Blume, Fabian; Karppi, Johanna; Koistinen, Antti E.; Schuiten, Eva; Voß, Moritz; Bornscheuer, Uwe; Deska, Jan; Master, Emma R.

In: ChemSusChem, 01.01.2019.

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@article{9cffd97b465b4d0c8b24b2adf27846fa,
title = "Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades",
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.",
keywords = "amination, biocatalysis, carbohydrates, domino reactions, enzymes",
author = "Ville Aumala and Filip Mollerup and Edita Jurak and Fabian Blume and Johanna Karppi and Koistinen, {Antti E.} and Eva Schuiten and Moritz Vo{\ss} and Uwe Bornscheuer and Jan Deska and Master, {Emma R.}",
note = "| openaire: EC/H2020/648925/EU//BHIVE",
year = "2019",
month = "1",
day = "1",
doi = "10.1002/cssc.201802580",
language = "English",
journal = "ChemSusChem",
issn = "1864-5631",
publisher = "Wiley-VCH Verlag",

}

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TY - JOUR

T1 - Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades

AU - Aumala, Ville

AU - Mollerup, Filip

AU - Jurak, Edita

AU - Blume, Fabian

AU - Karppi, Johanna

AU - Koistinen, Antti E.

AU - Schuiten, Eva

AU - Voß, Moritz

AU - Bornscheuer, Uwe

AU - Deska, Jan

AU - Master, Emma R.

N1 - | openaire: EC/H2020/648925/EU//BHIVE

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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.

AB - 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.

KW - amination

KW - biocatalysis

KW - carbohydrates

KW - domino reactions

KW - enzymes

UR - http://www.scopus.com/inward/record.url?scp=85060948148&partnerID=8YFLogxK

U2 - 10.1002/cssc.201802580

DO - 10.1002/cssc.201802580

M3 - Article

JO - ChemSusChem

JF - ChemSusChem

SN - 1864-5631

ER -

ID: 31993294