title: New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from Sorangium cellulosum So ce56.
abstract: Sesquiterpenes are natural products derived from the common precursor farnesyl pyrophosphate (FPP) but are highly diverse in structure and function. Cytochrome P450 enzymes (P450s) exhibit the unique ability to introduce molecular oxygen into non-activated C-H bonds. In plant biosynthetic pathways, P450s commonly derivatize sesquiterpene hydrocarbons. However, the potential of bacterial P450s for terpene derivatization is still underinvestigated. This work compares the substrate specificities and regioselectivities of the sesquiterpene hydroxylases CYP260A1 and CYP264B1 from myxobacterium Sorangium cellulosum So ce56. Four tested substrate classes (eremophilanes, humulanes, caryophyllanes, and cedranes) were converted by both P450s. The achievable variety of oxidations is demonstrated on the model substrates (+)-nootkatone and zerumbone. Increasing the number of functionally investigated P450s, this study represents a step towards the selective derivatization of sesquiterpenes.
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123, Saarbrücken, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Schifrin
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123, Saarbrücken, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Litzenburger
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123, Saarbrücken, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Ringle
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123, Saarbrücken, Germany.|Institute of Biotechnology, Vietnam Academy of Science and Technology (VAST), 18-Hoang Quoc Viet, Hanoi, Vietnam.
authors.forename: Thuy T B
authors.initials: TT
authors.lastname: Ly
authors.affiliation: Universität des Saarlandes, Biochemie, Campus B2.2, 66123, Saarbrücken, Germany. ritabern@mx.uni-saarland.de.
authors.forename: Rita
authors.initials: R
authors.lastname: Bernhardt
mesh_terms: D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D055162:Biocatalysis; D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D009231:Myxococcales / Q000201:enzymology*; D010084:Oxidation-Reduction; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D001426:Bacterial Proteins; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C403304:zerumbone; D003577:Cytochrome P-450 Enzyme System; C050302:nootkatone
keywords: cytochromes; enzyme catalysis; hydroxylation; regioselectivity; terpenoids