caa a22 4500 605504164 CHVBK 20210128100614.0 cr unu---uuuuu 210128e20150401xx s 000 0 eng 10.1007/s00253-014-6206-5 doi (NATIONALLICENCE)springer-10.1007/s00253-014-6206-5 Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H [Elektronische Daten] [Jeffery Shaw, Daniel Spakowicz, Rahul Dalal, Jared Davis, Nina Lehr, Brian Dunican, Esteban Orellana, Alexandra Narváez-Trujillo, Scott Strobel] An endophytic fungus was isolated that produces a series of volatile natural products, including terpenes and odd chain polyenes. Phylogenetic analysis of the isolate using five loci suggests that it is closely related to Nigrograna mackinnonii CBS 674.75. The main component of the polyene series was purified and identified as (3E,5E,7E)-nona-1,3,5,7-tetraene (NTE), a novel natural product. Non-oxygenated hydrocarbons of this chain length are uncommon and desirable as gasoline-surrogate biofuels. The biosynthetic pathway for NTE production was explored using metabolic labeling and gas chromatography time of flight mass spectometer (GCMS). Two-carbon incorporation 13C acetate suggests that it is derived from a polyketide synthase (PKS) followed by decarboxylation. There are several known mechanisms for such decarboxylation, though none have been discovered in fungi. Towards identifying the PKS responsible for the production of NTE, the genome of N. mackinnonii E5202H (ATCC SD-6839) was sequenced and assembled. Of the 32 PKSs present in the genome, 17 are predicted to contain sufficient domains for the production of NTE. These results exemplify the capacity of endophytic fungi to produce novel natural products that may have many uses, such as biologically derived fuels and commodity chemicals. Springer-Verlag Berlin Heidelberg, 2015 Endophyte nationallicence Natural product nationallicence Volatile organic compound nationallicence Polyene nationallicence Medium-chain hydrocarbon nationallicence Biofuel nationallicence Polyketide synthase nationallicence Shaw Jeffery Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Spakowicz Daniel Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Dalal Rahul Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Davis Jared Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Lehr Nina Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Dunican Brian Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Orellana Esteban Laboratorio de Biotecnología Vegetal, Pontificia Universidad Católica del Ecuador, Quito, Ecuador aut Narváez-Trujillo Alexandra Laboratorio de Biotecnología Vegetal, Pontificia Universidad Católica del Ecuador, Quito, Ecuador aut Strobel Scott Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut Applied Microbiology and Biotechnology Springer Berlin Heidelberg 99/8(2015-04-01), 3715-3728 0175-7598 99:8<3715 2015 99 253 https://doi.org/10.1007/s00253-014-6206-5 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00253-014-6206-5 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Shaw Jeffery Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Spakowicz Daniel Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Dalal Rahul Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Davis Jared Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Lehr Nina Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Dunican Brian Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 700 1- Orellana Esteban Laboratorio de Biotecnología Vegetal, Pontificia Universidad Católica del Ecuador, Quito, Ecuador aut NATIONALLICENCE 700 1- Narváez-Trujillo Alexandra Laboratorio de Biotecnología Vegetal, Pontificia Universidad Católica del Ecuador, Quito, Ecuador aut NATIONALLICENCE 700 1- Strobel Scott Department of Molecular Biophysics and Biochemistry, Yale University, 06511, New Haven, CT, USA aut NATIONALLICENCE 773 0- Applied Microbiology and Biotechnology Springer Berlin Heidelberg 99/8(2015-04-01), 3715-3728 0175-7598 99:8<3715 2015 99 253