Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water

Hinzmann A, Betke T, Asano Y, Gröger H (Accepted)
Chemistry - A European Journal.

Zeitschriftenaufsatz | Angenommen | Englisch
 
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Abstract / Bemerkung
While belonging to the most fundamental functional groups, nitriles represent a class of compound still raising challenges in terms of an efficient, cost-effective and at the same time sustainable way for their synthesis. Complementing existing chemical routes recently a cyanide-free enzymatic process technology based on the use of an aldoxime dehydratase (Oxd) as biocatalyst component has been developed and successfully applied for a range of nitrile products. In these biotransformations, these Oxd enzymes catalyze the dehydration of aldoximes as readily available substrates to the desired nitrile products. Within this concept article these developments with such enzymes are summarized with a strong focus on the synthetic application side. By means of the achieved synthetic examples, it will be demonstrated that this biocatalytic technology has the potential to "cross the bridge" between the production of fine chemicals and pharmaceuticals on the one hand and bulk and commodity chemicals on the other hand. For example, Oxd enzymes were found to give high enantioselectivities and can give access to both enantiomers when starting either from the ( E )- or ( Z )-aldoxime racemate. However, besides their high potential towards stereoselective synthesis making the attractive for the area of fine chemicals and pharmaceuticals, Oxd enzymes also turned out to suitable for the dehydration of a range of aldoximes derived from aliphatic achiral commodity chemicals, leading to the corresponding nitriles, e.g., adiponitrile and fatty nitriles, with high substrate loading up to the Kg per L range as a required criteria for the field of bulk chemicals production. © 2020 Wiley-VCH GmbH.
Erscheinungsjahr
2020
Zeitschriftentitel
Chemistry - A European Journal
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2948404

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Hinzmann A, Betke T, Asano Y, Gröger H. Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water. Chemistry - A European Journal. Accepted.
Hinzmann, A., Betke, T., Asano, Y., & Gröger, H. (Accepted). Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water. Chemistry - A European Journal. https://doi.org/10.1002/chem.202001647
Hinzmann, A., Betke, T., Asano, Y., and Gröger, H. (Accepted). Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water. Chemistry - A European Journal.
Hinzmann, A., et al., Accepted. Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water. Chemistry - A European Journal.
A. Hinzmann, et al., “Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water”, Chemistry - A European Journal, Accepted.
Hinzmann, A., Betke, T., Asano, Y., Gröger, H.: Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water. Chemistry - A European Journal. (Accepted).
Hinzmann, Alessa, Betke, Tobias, Asano, Yasuhisa, and Gröger, Harald. “Synthetic processes towards nitriles without cyanide: A biocatalytic concept based on dehydration of aldoximes in water”. Chemistry - A European Journal (Accepted).
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