Carboligation of 5-(hydroxymethyl)furfural via whole-cell catalysis to form C12 furan derivatives and their use for hydrazone formation

Microbial Cell Factories

Research

Dörte Rother¹  Nicola Rehnberg²  Sara Jonsdottir Glaser³  Sang-Hyun Pyo³  Rajni Hatti-Kaul³ 

[1] Bona Sweden AB, Box 210 74, SE-200 21, Malmö, Sweden;Centre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, SE-22100, Lund, Sweden;Institute for Bio- and Geosciences 1: Biotechnology, Forschungszentrum Jülich GmbH, 52425, Jülich, Germany;Division of Biotechnology, Department of Chemistry, Center for Chemistry and Chemical Engineering, Lund University, 22100, Lund, Sweden;

关键词: 5-(hydroxymethyl)furfural;    5,5’-bis(hydroxymethyl)furoin (DHMF);    5,5’-bis(hydroxymethyl)furil (BHMF);    Whole-cell biocatalyst;    Benzaldehyde lyase;    Hydrazone;   

DOI  :  10.1186/s12934-023-02130-1

 received in 2023-05-06, accepted in 2023-06-22,  发布年份 2023

来源: Springer

【 摘 要 】

BackgroundBiobased 5-(hydroxymethyl)furfural (5-HMF) is an important platform that offers numerous possibilities for upgrading to a range of chemical, material and fuel products. One reaction of special interest is the carboligation of 5-HMF into C12 compounds, including 5,5’-bis(hydroxymethyl)furoin (DHMF) and its subsequent oxidation to 5,5’-bis(hydroxymethyl)furil (BHMF), due to their potential applications as building blocks for polymers and hydrocarbon fuels.ObjectivesThis study was aimed at evaluating the use of whole cells of Escherichia coli carrying recombinant Pseudomonas fluorescens benzaldehyde lyase as biocatalysts for 5-HMF carboligation, recovery of the C12 derivatives DHMF and BHMF, and testing the reactivity of the carbonyl groups for hydrazone formation for potential use as cross-linking agents in surface coatings. The effects of different parameters on the reaction were investigated to find the conditions for achieving high product yield and productivity.ResultsThe reaction with 5 g/L 5-HMF using 2 gCDW/L recombinant cells in 10% dimethyl carbonate, pH 8.0 at 30 °C resulted in DHMF yield of 81.7% (0.41 mol/mol) at 1 h, and BHMF yield of 96.7% (0.49 mol/mol) at 72 h reaction time. Fed-batch biotransformation generated a maximum DHMF concentration of 53.0 g/L (or 26.5 g DHMF/g cell catalyst) with productivity of 10.6 g/L.h, after five feeds of 20 g/L 5-HMF. Both DHMF and BHMF reacted with adipic acid dihydrazide to form hydrazone that was confirmed by Fourier-transform infrared spectroscopy and 1H NMR.ConclusionThe study demonstrates the potential application of recombinant E. coli cells for cost-effective production of commercially relevant products.

【 授权许可】

CC BY   
© The Author(s) 2023

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