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Biocatalytic Synthesis of Two Furan-Based Amino Compounds 2-Acetyl-4-aminofuran and 3-Acetylamino-5-(α-aminoethyl)-furan from Chitin Resources

ACS Sustainable Chemistry & Engineering [2024]
Chaoqiang Wu, Xin Zhang, Wei Liu, Chengyong Wang, Qianqian Jiang, Feifei Chen, Quanzhen Liu, Fei Cao, Gaowei Zheng, Alei Zhang, Kequan Chen
ABSTRACT

Chitin, as the second most abundant biomass in nature, possesses 7 wt % biologically fixed nitrogen, and its direct valorization into valuable nitrogen (N)-containing chemicals is optimal. Herein, we report the biosynthesis of two specific furan-based amine compounds, 2-acetyl-4-aminofuran (2A4AF) and 3-acetylamino-5-(α-aminoethyl)-furan (3A5AEF), from chitin-derived 3-acetamido-5-acetylfuran (3A5AF) via biocatalytic deacetylation and reduction amination, respectively. An amidase (MmH) from Starkeya sp. and an R-selective aminotransferase (ATA117) from Arthrobacter sp. were obtained, which can, respectively, convert 3A5AF to 2A4AF with a yield of 79.3% (47.58 mM) and (R)-3A5AEF (enantiomeric excess (ee) value of >99%) with a yield of 84.0% (126 mM), respectively, under the optimal conditions. The biosynthesis efficiency of the two amines was high in comparison with chemical approaches. This work paves the way for green and efficient production of furan-based amino chemicals from inexpensive renewable chitin resources.

MATERIALS

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