An Ancient Relative of Cyclooxygenase in Cyanobacteria Is a Linoleate 10S-Dioxygenase That Works in Tandem with a Catalase-related Protein with Specific 10S-Hydroperoxide Lyase Activity
作者： Alan R. Brash , Narayan P. Niraula , William E. Boeglin , Zahra Mashhadi
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摘要: In the course of exploring scope catalase-related hemoprotein reactivity toward fatty acid hydroperoxides, we detected a novel candidate in cyanobacterium Nostoc punctiforme PCC 73102. The immediate neighboring upstream gene, annotated as "cyclooxygenase-2," appeared to be potential heme dioxygenase. We cloned both genes and expressed cDNAs Escherichia coli, confirming their character. Oxygen electrode recordings demonstrated rapid (>100 turnovers/s) reaction dioxygenase with oleic linoleic acids. HPLC, including chiral column analysis, UV, GC-MS oxygenated products, identified 10S-dioxygenase activity. reacted rapidly specifically linoleate 10S-hydroperoxide (>2,500 hydroperoxide lyase activity specific for 10S-hydroperoxy enantiomer. products were by NMR (8E)10-oxo-decenoic C8 fragments, 1-octen-3-ol 2Z-octen-1-ol, ∼3:1 ratio. Chiral HPLC analysis established strict enzymatic control formation 3R alcohol configuration (99% enantiomeric excess) contrasted racemic formed hematin or ferrous ions. 10S-dioxygenase, sequence which contains signature catalytic cyclooxygenases fungal dioxygenases (YRWH), appears ancestor. expands known reactions proteins functions transformation 10S-hydroperoxylinoleate.
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