Abstract
2-Furonitrile is an interesting nitrile product for the chemical industry due to its use as intermediate in the field of fine chemicals and pharmaceuticals or as a potential sweetener, as well as due to its access from biorenewables. As an alternative to current processes based on, e.g., the ammoxidation of furfural with ammonia as a gas phase reaction running at > 400 °C, we recently reported an enzymatic dehydration of 2-furfuryl aldoxime being obtained easily from furfural and hydroxylamine. However, improving the catalytic properties of the aldoxime dehydratase biocatalyst from Rhodococcus sp. YH3-3 (OxdYH3-3) in terms of activity and stability remained a challenge. In this contribution, the successful development of aldoxime dehydratase OxdYH3-3 mutants that were generated by directed evolution and its enhanced activity toward 2-furfuryl aldoxime is reported. The mutant OxdYH3-3 N266S showed an improved activity of up to six times higher than the wild type when utilizing a substrate concentration of 50–100 mM of 2-furfuryl aldoxime.
Highlights
The tasks for realizing access to industrial chemicals from biorenewables on scale include the development of approaches for aromatic compounds as well as for nitriles starting from bio-based raw materials and ideally waste-materials [1]. 2-Furonitrile, being known as intermediate in the field of fine chemicals and pharmaceuticals or as a potential sweetener [2], combines these two compound classes
It is noteworthy that in these biotransformations the mutant OxdYH3-3 N266S turned out to be superior over the wild-type enzyme and gave a three times (54%) and eight times (40%) higher conversion when comparing the data for the reactions running at 50 mM of E-3-pyridine and 2-furfuryl aldoxime after a reaction time of 1 h, respectively (Figure 3)
OxdYH3-3 in E.coli BL21(DE3) that were generated by directed evolution and its enhanced activity toward 2-furfuryl aldoxime has been reported
Summary
The tasks for realizing access to industrial chemicals from biorenewables on scale include the development of approaches for aromatic compounds as well as for nitriles starting from bio-based raw materials and ideally waste-materials [1]. 2-Furonitrile, being known as intermediate in the field of fine chemicals and pharmaceuticals or as a potential sweetener (due to an about thirty-fold higher sweetening power compared to sucrose) [2], combines these two compound classes. The tasks for realizing access to industrial chemicals from biorenewables on scale include the development of approaches for aromatic compounds as well as for nitriles starting from bio-based raw materials and ideally waste-materials [1]. 2-Furonitrile, being known as intermediate in the field of fine chemicals and pharmaceuticals or as a potential sweetener (due to an about thirty-fold higher sweetening power compared to sucrose) [2], combines these two compound classes. The availability of 2-furfural from natural waste sources makes its utilization attractive for the synthesis of derivatives with industrial potential [1,3]. Furfural is obtained by an acid-catalyzed dehydration of cellulose biomass, and its derivatives containing nitrogen atoms have interesting features, such as the ability of furfurylamine to be used in the pharmaceutical synthesis or resin industry [4,5,6,7]. The preparation of 2-furonitrile from furfural through ammoxidation requires reaction temperatures exceeding 400 ◦ C [2], whereas other procedures that are conducted on lab scale revealed to be tedious [8,9,10,11,12]
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