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Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid
journal contribution
posted on 2023-05-17, 22:00 authored by Amos, RIJ, Gourlay, BS, Brian YatesBrian Yates, Schiesser, CH, Trevor LewisTrevor Lewis, Jason SmithJason SmithAryl hydrazides are oxidised to acyl radicals through a mechanism involving diimide intermediates that are prone to nucleophilic acyl substitution. This oxidation occurs regardless of the oxidant involved, however there is no evidence that the acyl radical formed undergoes further oxidation to the corresponding acylium ion, even in the presence of strong oxidants. This study may provide insight into the mechanism of isoniazid resistance in Mycobacterium tuberculosis.
History
Publication title
Organic and Biomolecular ChemistryVolume
11Pagination
170-176ISSN
1477-0520Department/School
School of Natural SciencesPublisher
RSC PublicationsPlace of publication
Thomas Graham House, Science Park, Milton Rd, Cambridge, England, Cambs, Cb4 0WfRights statement
Copyright 2013 Royal Society of ChemistryRepository Status
- Open