Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• ], and recently it was reported that so called photopyrones (8–15) act as signaling molecules in the cell–cell communication system of the bacterium Photorhabdus luminescens (Figure 1) [14]. Since the biological activities of α-pyrones are very diverse, these compounds are in the focus of synthetic

• function for α-pyrones within bacteria was discovered. The so called photopyrones (8–15, Figure 1) represent extracellular signals involved in cell–cell communication [14]. Photorhabdus luminescens, an entomopathogenic bacterium species, excretes these molecules, and binding of the latter to the respective

• molecules, e.g., photopyrones (8–15) from Photorhabdus luminescens are synthesized by such a head-to-head condensation of two acyl moieties [60]. Also the csypyrones (79–81, Figure 21), first reported from Aspergillus oryzae, are composed of two independent chains which are interconnected thereafter [85

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, doi:10.3762/bjoc.11.152

• , 60438 Frankfurt am Main, Germany 10.3762/bjoc.11.152 Abstract 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

• 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. Keywords: cell–cell communication; ketosynthase; photopyrones; pseudopyronines; quorum

• [5] and selective COX-2 inhibitors [6]. Recently, it was shown that photopyrones (Figure 1) are signaling molecules in a new cell–cell communication system in the entomopathogenic bacterium Photorhabdus luminescens. The system consists of endogenously produced photopyrones as signaling molecules and