Directing Biosynthesis VI - Book of abstracts

Elucidation of the crystal structure of the clorothricin decalin synthase of Streptomyces antibioticus Monserrat Manzo Ruiz, Catherine R. Back, Nicholas J. Burton, Paul R. Race University of Bristol, UK Introduction: Streptomyces antibioticus produces the spirotetonate antibiotic chlorothricin 1 . The biosynthesis of this natural product involves two cyclisation reactions, one of which is catalyzed by the enzyme ChlE3 and forms the distinctive trans -decalin ring of this compound 2 . To understand this reaction the crystal structure of ChlE3 has been determined. Methods: ChlE3 was cloned into pET29b. E. coli BL21 (DE3) was used for protein expression, 1 mM IPTG was added for induction, incubating at 20°C for 16 hrs. ChlE3 was purified through nickel column and further size exclusion chromatography. Crystallisation trials were established using the sitting drop method. Results and conclusions: Multiple large yellow crystals appeared in a range of different conditions, the best diffraction data was obtained from a crystal grown in lithium chloride, PEG and Tris-HCl. Diffraction data were collected at Diamond Light Source using beamline I24. The structure of ChlE3 was determined by molecular replacement and refined to 1.92 Å resolution. An overall completeness of 99.9% was achieved with a multiplicity of 6.5. Inspection of the ChlE3 structure reveals the presence of an active site bound flavin adenine dinucleotide (FAD) cofactor and implies a mechanism for intramolecular [4+2] cycloaddition in this biocatalyst. References 1. Jia, X. Y.; Tian, Z. H.; Shao, L.; Qu, X. D.; Zhao, Q. F.; Tang, J.; Tang, G. L.; Liu, W. Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis. Chem Biol. 2006, 13 (6), 575-85. DOI:10.1016/j.chembiol.2006.03.008 2. Tian, Z.; Sun, P.; Yan, Y.; Wu, Z.; Zheng, Q.; Zhou, S.; Zhang, H.; Yu, F.; Jia, X.; Chen, D.; Mándi, A.; Kurtán, T.; Liu, W. An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins. Nat Chem Biol. 2015, 11 (4), 259-65. DOI:10.1038/nchembio.1769

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