Conversion of Aldehyde to Alkane by a Peroxoiron(III) Complex: A Functional Model for the Cyanobacterial Aldehyde-Deformylating Oxygenase

Alireza Shokri, Lawrence Que

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20 Scopus citations

Abstract

Cyanobacterial aldehyde-deformylating oxygenase (cADO) converts long-chain fatty aldehydes to alkanes via a proposed diferric-peroxo intermediate that carries out the oxidative deformylation of the substrate. Herein, we report that the synthetic iron(III)-peroxo complex [FeIII2-O2)(TMC)]+ (TMC = tetramethylcyclam) causes a similar transformation in the presence of a suitable H atom donor, thus serving as a functional model for cADO. Mechanistic studies suggest that the H atom donor can intercept the incipient alkyl radical formed in the oxidative deformylation step in competition with the oxygen rebound step typically used by most oxygenases for forming C-O bonds. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)7686-7691
Number of pages6
JournalJournal of the American Chemical Society
Volume137
Issue number24
DOIs
StatePublished - Jun 24 2015

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