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Transketolase Catalyzed Synthesis of N ‐Aryl Hydroxamic Acids

Abstract : 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.
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https://hal.uca.fr/hal-03607724
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Submitted on : Monday, March 14, 2022 - 11:06:00 AM
Last modification on : Tuesday, March 15, 2022 - 3:37:44 AM

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Inés Fúster Fernández, Laurence Hecquet, Wolf‐dieter Fessner. Transketolase Catalyzed Synthesis of N ‐Aryl Hydroxamic Acids. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2022, 364 (3), pp.612-621. ⟨10.1002/adsc.202101100⟩. ⟨hal-03607724⟩

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