Transketolase Catalyzed Synthesis of N‐Aryl Hydroxamic Acids

Hydroxamic acids are metal‐chelating compounds that show important biological activity including anti‐tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non‐natural acceptor substrate. Realizing the structural and elec...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-02, Vol.364 (3), p.612-621
Main Authors: Fúster Fernández, Inés, Hecquet, Laurence, Fessner, Wolf‐Dieter
Format: Article
Language:English
Subjects:
Acids
Aromatic compounds
Benzaldehyde
biocatalysis
Biological activity
Carbon
Chelation
Chemical Sciences
Chemical synthesis
Conversion
C−N ligation
hydroxamic acid
iron(III) chelation
Nitrogen
nitrosoarenes
Substrates
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Summary:Hydroxamic acids are metal‐chelating compounds that show important biological activity including anti‐tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non‐natural acceptor substrate. Realizing the structural and electronic similarity to nitrosobenzene, we studied the TK‐catalyzed conversion of nitrosoarenes to yield N‐arylated hydroxamic acids. Here we demonstrate that wild‐type and variants of this versatile TKgst enzyme indeed induce the rapid biocatalytic conversion of variously p‐, m‐ and o‐substituted nitrosoarenes to produce a variety of corresponding N‐aryl hydroxamic acids via creation of a carbon‐nitrogen instead of a carbon‐carbon bond. Further structural modifications can be introduced by varying the donor component, such as hydroxypyruvate or pyruvate.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101100