Radical Ring-Opening Reaction of Non-Activated Oximes Catalyzed by Aldoxime Dehydratases.

ABSTRACT: The iminyl radical is a distinctive N-centered radical which serves as a versatile synthon in preparation of nitrogen-containing compounds. In principle, iminyl radicals can be directly generated by single electron reduction of oximes through elimination of OH group. However, due to the low reactivity of the oxime N─OH bonds, direct conversion of the oximes does not proceed efficiently, thereby enforcing chemical activation of the oxime OH group which results in the formation of stoichiometric by-products. To overcome this problem, we are developing a new biocatalytic system using aldoxime dehydratases. Through a series of enzyme screenings, we identified an aldoxime dehydratase from N. simplex (NsOxd) which is capable of catalyzing iminyl radical-mediated ring-opening reactions. Notably,

SUBMITTER: Kato S 

PROVIDER: S-EPMC12582005 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature