Literature DB >> 23514600

Probing the mechanism of cyanobacterial aldehyde decarbonylase using a cyclopropyl aldehyde.

Bishwajit Paul1, Debasis Das, Benjamin Ellington, E Neil G Marsh.   

Abstract

Cyanobacterial aldehyde decarbonylase (cAD) is a non-heme diiron oxygenase that catalyzes the conversion of fatty aldehydes to alkanes and formate. The mechanism of this chemically unusual reaction is poorly understood. We have investigated the mechanism of C1-C2 bond cleavage by cAD using a fatty aldehyde that incorporates a cyclopropyl group, which can act as a radical clock. When reacted with cAD, the cyclopropyl aldehyde produces 1-octadecene as the rearranged product, providing evidence for a radical mechanism for C-C bond scission. In an alternate pathway, the cyclopropyl aldehyde acts as a mechanism-based irreversible inhibitor of cAD through covalent binding of the alkyl chain to the enzyme.

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Year:  2013        PMID： 23514600      PMCID： PMC3651851          DOI： 10.1021/ja3115949

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


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