TY - JOUR A1 - Kresovic, Darko A1 - Schempp, Florence A1 - Cheikh-Ali, Zakaria A1 - Bode, Helge B. T1 - A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis JF - Beilstein Journal of Organic Chemistry PY - 2015/// VL - 11 SP - 1412 EP - 1417 SN - 1860-5397 DO - 10.3762/bjoc.11.152 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.11.152 KW - cell–cell communication KW - ketosynthase KW - photopyrones KW - pseudopyronines KW - quorum sensing N2 - The biosynthesis of photopyrones, novel quorum sensing signals in Photorhabdus, has been studied by heterologous expression of the photopyrone synthase PpyS catalyzing the head-to-head condensation of two acyl moieties. The biochemical mechanism of pyrone formation has been investigated by amino acid exchange and bioinformatic analysis. Additionally, the evolutionary origin of PpyS has been studied by phylogenetic analyses also revealing homologous enzymes in Pseudomonas sp. GM30 responsible for the biosynthesis of pseudopyronines including a novel derivative. Moreover this novel class of ketosynthases is only distantly related to other pyrone-forming enzymes identified in the biosynthesis of the potent antibiotics myxopyronin and corallopyronin. ER -