Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades

Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades
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DOI:
10.1002/cssc.201802580
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发表时间:
2019-02-21
期刊:
影响因子:
8.4
通讯作者:
Master, Emma R.
Master, Emma R.
中科院分区:
化学2区
文献类型:
--
作者:
Aumala, Ville;Mollerup, Filip;Master, Emma R.

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植物性碳水化合物是一种丰富的可再生资源。将碳水化合物转化为新产品,包括用于生物材料应用的胺功能化构建块,可以降低对化石资源的依赖。本文展示了氨基碳水化合物(包括低聚糖)的生物催化生产途径。在每种情况下,采用两步生物催化来功能化含d-半乳糖的碳水化合物,分别使用来自谷物镰刀菌的半乳糖氧化酶或来自双孢蘑菇的吡喃糖脱氢酶,然后使用来自紫色色杆菌的ω -转氨酶(csi - ω - ta)。质谱法证实了6-氨基-6-脱氧-d-半乳糖、2-氨基-2-脱氧-d-半乳糖和2-氨基-2-脱氧-6-醛-d-半乳糖的形成。Cvi-omega-TA对6-醛-d-半乳糖的活性最高,在同时氧化d-半乳糖和转氨化6-醛-d-半乳糖的反应中,6-氨基-6-脱氧d-半乳糖的产率最高(67%)。
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.