title: Characterization of the gene cluster CYP264B1-geoA from Sorangium cellulosum So ce56: biosynthesis of (+)-eremophilene and its hydroxylation.
abstract: Terpenoids can be found in almost all forms of life; however, the biosynthesis of bacterial terpenoids has not been intensively studied. This study reports the identification and functional characterization of the gene cluster CYP264B1-geoA from Sorangium cellulosum So ce56. Expression of the enzymes and synthesis of their products for NMR analysis and X-ray diffraction were carried out by employing an Escherichia coli whole-cell conversion system that provides the geoA substrate farnesyl pyrophosphate through simultaneous overexpression of the mevalonate pathway genes. The geoA product was identified as a novel sesquiterpene, and assigned NMR signals unambiguously proved that geoA is an (+)-eremophilene synthase. The very tight binding of (+)-eremophilene (∼0.40 μM), which is also available in S. cellulosum So ce56, and its oxidation by CYP264B1 suggest that the CYP264B1-geoA gene cluster is required for the biosynthesis of (+)-eremophilene derivatives.
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123 Saarbrücken (Germany).
authors.forename: Alexander
authors.initials: A
authors.lastname: Schifrin
authors.forename: Thuy T B
authors.initials: TT
authors.lastname: Ly
authors.forename: Nils
authors.initials: N
authors.lastname: Günnewich
authors.forename: Josef
authors.initials: J
authors.lastname: Zapp
authors.forename: Verena
authors.initials: V
authors.lastname: Thiel
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
authors.forename: Frank
authors.initials: F
authors.lastname: Hannemann
authors.forename: Yogan
authors.initials: Y
authors.lastname: Khatri
authors.forename: Rita
authors.initials: R
authors.lastname: Bernhardt
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000235:genetics / Q000378:metabolism; D003001:Cloning, Molecular; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics* / Q000378:metabolism*; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D005656:Fungal Proteins / Q000235:genetics / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008798:Mevalonic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D015394:Molecular Structure; D005810:Multigene Family; D009231:Myxococcales / Q000235:genetics* / Q000378:metabolism*; D000072516:Retinoic Acid 4-Hydroxylase; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D014961:X-Ray Diffraction
chemical_list: D005656:Fungal Proteins; D012717:Sesquiterpenes; C015367:mevalonolactone; D003577:Cytochrome P-450 Enzyme System; D000072516:Retinoic Acid 4-Hydroxylase; D019883:Alkyl and Aryl Transferases; C108877:terpene synthase; D008798:Mevalonic Acid
keywords: Sorangium cellulosum So ce56; cytochromes; eremophilenes; hydroxylation; terpenes