A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis

Darko Kresovic, Florence Schempp, Zakaria Cheikh-Ali and Helge B. Bode
Beilstein J. Org. Chem. 2015, 11, 1412–1417. https://doi.org/10.3762/bjoc.11.152

Supporting Information

Supporting Information File 1: Experimental procedures, details of bioinformatic analysis and NMR data of pseudopyronines.
Format: PDF Size: 1.5 MB Download

Cite the Following Article

A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis
Darko Kresovic, Florence Schempp, Zakaria Cheikh-Ali and Helge B. Bode
Beilstein J. Org. Chem. 2015, 11, 1412–1417. https://doi.org/10.3762/bjoc.11.152

How to Cite

Kresovic, D.; Schempp, F.; Cheikh-Ali, Z.; Bode, H. B. Beilstein J. Org. Chem. 2015, 11, 1412–1417. doi:10.3762/bjoc.11.152

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Hussain, A.; Sravanthi, R.; Katta, S.; Ramachary, D. B. Two-step, high-yielding total synthesis of antibiotic pyrones. Organic & biomolecular chemistry 2024, 22, 554–560. doi:10.1039/d3ob01923c
  • Liu, X.; Wang, Y.; Zaleta-Pinet, D. A.; Borris, R. P.; Clark, B. R. Antibacterial and Anti-Biofilm Activity of Pyrones from a Pseudomonas mosselii Strain. Antibiotics (Basel, Switzerland) 2022, 11, 1655. doi:10.3390/antibiotics11111655
  • Lu, Y.; Liu, X.; Lotfy, R.; Liu, S.; Tesfa, A. F.; Wolber, G.; Bureik, M.; Clark, B. R. Experimental and Computational Studies on the Biotransformation of Pseudopyronines with Human Cytochrome P450 CYP4F2. Journal of natural products 2022, 85, 2603–2609. doi:10.1021/acs.jnatprod.2c00616
  • Martins, T. P.; Glasser, N. R.; Kountz, D. J.; Oliveira, P.; Balskus, E. P.; Leão, P. N. Biosynthesis of the Unusual Carbon Skeleton of Nocuolin A. ACS chemical biology 2022, 17, 2528–2537. doi:10.1021/acschembio.2c00464
  • Banerjee, A.; Saha, S. Antimicrobial Peptide and Toxin-Based Mutualism: Obligate Symbiotic Entomopathogenic Nematode—Bacterium Associations. Microbes in Microbial Communities; Springer Singapore, 2021; pp 91–114. doi:10.1007/978-981-16-5617-0_4
  • Zhou, S.; Hao, T.; Xu, S.; Deng, Y. Coenzyme A thioester-mediated carbon chain elongation as a paintbrush to draw colorful chemical compounds. Biotechnology advances 2020, 43, 107575. doi:10.1016/j.biotechadv.2020.107575
  • Wang, W.-G.; Wang, H.; Du, L.-Q.; Li, M.; Chen, L.; Yu, J.; Cheng, G.-G.; Zhan, M.-T.; Hu, Q.-F.; Zhang, L.; Yao, M.; Matsuda, Y. Molecular Basis for the Biosynthesis of an Unusual Chain-Fused Polyketide, Gregatin A. Journal of the American Chemical Society 2020, 142, 8464–8472. doi:10.1021/jacs.0c02337
  • Lixia, P.; Dengfeng, Y. Novel Ketosynthases Catalyzing the Non-Decarboxylative Claisen Condensation. Mini-Reviews in Organic Chemistry 2020, 17, 169–175. doi:10.2174/1570193x16666191002155136
  • Nofiani, R.; Philmus, B.; Nindita, Y.; Mahmud, T. 3-Ketoacyl-ACP synthase (KAS) III homologues and their roles in natural product biosynthesis. MedChemComm 2019, 10, 1517–1530. doi:10.1039/c9md00162j
  • Balzano, S.; Villanueva, L.; de Bar, M. W.; Canavesi, D. X. S.; Yildiz, C.; Engelmann, J. C.; Maréchal, E.; Lupette, J.; Damsté, J. S. S.; Schouten, S. Biosynthesis of Long Chain Alkyl Diols and Long Chain Alkenols in Nannochloropsis spp. (Eustigmatophyceae). Plant & cell physiology 2019, 60, 1666–1682. doi:10.1093/pcp/pcz078
  • Zhang, D.; Zhang, F.; Liu, W. A KAS-III Heterodimer in Lipstatin Biosynthesis Nondecarboxylatively Condenses C 8 and C 14 Fatty Acyl-CoA Substrates by a Variable Mechanism during the Establishment of a C 22 Aliphatic Skeleton. Journal of the American Chemical Society 2019, 141, 3993–4001. doi:10.1021/jacs.8b12843
  • Jensen, M. R.; Goblirsch, B. R.; Christenson, J. K.; Esler, M. A.; Mohamed, F. A.; Wackett, L. P.; Wilmot, C. M. OleA Glu117 is key to condensation of two fatty-acyl coenzyme A substrates in long-chain olefin biosynthesis. The Biochemical journal 2017, 474, 3871–3886. doi:10.1042/bcj20170642
  • Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis. Chemical reviews 2017, 117, 5521–5577. doi:10.1021/acs.chemrev.6b00697
  • Mori, T.; Awakawa, T.; Shimomura, K.; Saito, Y.; Yang, D.; Morita, H.; Abe, I. Structural Insight into the Enzymatic Formation of Bacterial Stilbene. Cell chemical biology 2016, 23, 1468–1479. doi:10.1016/j.chembiol.2016.10.010
  • Brameyer, S.; Heermann, R. Quorum Sensing and LuxR Solos in Photorhabdus. Current topics in microbiology and immunology 2016, 402, 103–119. doi:10.1007/82_2016_28
  • Goblirsch, B. R.; Jensen, M. R.; Mohamed, F. A.; Wackett, L. P.; Wilmot, C. M. Substrate Trapping in Crystals of the Thiolase OleA Identifies Three Channels That Enable Long Chain Olefin Biosynthesis. The Journal of biological chemistry 2016, 291, 26698–26706. doi:10.1074/jbc.m116.760892
  • Kancharla, P.; Bonnett, S. A.; Reynolds, K. A. Stenotrophomonas maltophilia OleC-Catalyzed ATP-Dependent Formation of Long-Chain Z-Olefins from 2-Alkyl-3-hydroxyalkanoic Acids. Chembiochem : a European journal of chemical biology 2016, 17, 1426–1429. doi:10.1002/cbic.201600063
  • Fisch, K. M.; Schäberle, T. F. Toolbox for Antibiotics Discovery from Microorganisms. Archiv der Pharmazie 2016, 349, 683–691. doi:10.1002/ardp.201600064
  • Schäberle, T. F. Biosynthesis of α-pyrones. Beilstein journal of organic chemistry 2016, 12, 571–588. doi:10.3762/bjoc.12.56
  • Bozhüyük, K. A. J.; Zhou, Q.; Engel, Y.; Heinrich, A. K.; Pérez, A. J.; Bode, H. B. Natural Products from Photorhabdus and Other Entomopathogenic Bacteria. Current topics in microbiology and immunology 2016, 402, 55–79. doi:10.1007/82_2016_24
Other Beilstein-Institut Open Science Activities