title: Terminal olefin (1-alkene) biosynthesis by a novel p450 fatty acid decarboxylase from Jeotgalicoccus species.
abstract: Terminal olefins (1-alkenes) are natural products that have important industrial applications as both fuels and chemicals. However, their biosynthesis has been largely unexplored. We describe a group of bacteria, Jeotgalicoccus spp., which synthesize terminal olefins, in particular 18-methyl-1-nonadecene and 17-methyl-1-nonadecene. These olefins are derived from intermediates of fatty acid biosynthesis, and the key enzyme in Jeotgalicoccus sp. ATCC 8456 is a terminal olefin-forming fatty acid decarboxylase. This enzyme, Jeotgalicoccus sp. OleT (OleT(JE)), was identified by purification from cell lysates, and its encoding gene was identified from a draft genome sequence of Jeotgalicoccus sp. ATCC 8456 using reverse genetics. Heterologous expression of the identified gene conferred olefin biosynthesis to Escherichia coli. OleT(JE) is a P450 from the cyp152 family, which includes bacterial fatty acid hydroxylases. Some cyp152 P450 enzymes have the ability to decarboxylate and to hydroxylate fatty acids (in α- and/or β-position), suggesting a common reaction intermediate in their catalytic mechanism and specific structural determinants that favor one reaction over the other. The discovery of these terminal olefin-forming P450 enzymes represents a third biosynthetic pathway (in addition to alkane and long-chain olefin biosynthesis) to convert fatty acid intermediates into hydrocarbons. Olefin-forming fatty acid decarboxylation is a novel reaction that can now be added to the catalytic repertoire of the versatile cytochrome P450 enzyme family.
authors.affiliation: LS9, Inc., 600 Gateway Blvd., South San Francisco, CA 94080, USA.
authors.forename: Mathew A
authors.initials: MA
authors.lastname: Rude
authors.forename: Tarah S
authors.initials: TS
authors.lastname: Baron
authors.forename: Shane
authors.initials: S
authors.lastname: Brubaker
authors.forename: Murtaza
authors.initials: M
authors.lastname: Alibhai
authors.forename: Stephen B
authors.initials: SB
authors.lastname: Del Cardayre
authors.forename: Andreas
authors.initials: A
authors.lastname: Schirmer
mesh_terms: D000475:Alkenes / Q000378:metabolism*; D002262:Carboxy-Lyases / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism*; D003001:Cloning, Molecular; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004926:Escherichia coli / Q000235:genetics; D005227:Fatty Acids / Q000378:metabolism*; D015870:Gene Expression; D008958:Models, Molecular; D008969:Molecular Sequence Data; D011994:Recombinant Proteins / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism; D017422:Sequence Analysis, DNA; D040141:Staphylococcaceae / Q000201:enzymology*
chemical_list: D000475:Alkenes; D004269:DNA, Bacterial; D005227:Fatty Acids; D011994:Recombinant Proteins; D002262:Carboxy-Lyases