Formal Synthesis of Galantinic Acid by Oxo‐Diels–Alder Methodology

Chaładaj, Wojciech; Jurczak, Janusz

doi:10.1002/ejoc.201001296

Cited by 8 publications

(1 citation statement)

References 32 publications

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“…This polyol amino acid has been also reported as a component of galantin I with a (3 S ,5 S ,6 S ) configuration and of the siderophore anachelin H with a (3 R ,5 S ,6 S ) configuration . Gla has already been the target of numerous synthesis approaches. − …”

Section: Resultsmentioning

confidence: 93%

Total Synthesis and Biological Evaluation of Paenilamicins from the Honey Bee Pathogen Paenibacillus larvae

et al. 2021

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Paenilamicins are a group of complex polycationic peptide secondary metabolites with antibacterial and antifungal activities produced by the devastating honey bee brood pathogen Paenibacillus larvae causing the lethal brood disease American Foulbrood (AFB). Here, we report the convergent total synthesis and structural revision of paenilamicin B2. Specific stereoisomers of paenilamicin B2 were synthesized for unambiguous confirmation of the natural product structure and for evaluation of biological activities. These studies revealed the N-terminal fragment of paenilamicin as an important pharmacophore. Infection assays using bee larvae and the insect pathogen Bacillus thuringiensis demonstrated that paenilamicins outcompete bacterial competitors in the ecological niche of P. larvae. Finally, we show first data that classifies paenilamicins as potential ribosome inhibitors. Hence, our synthesis route is a further step for understanding the pathogenicity of P. larvae and for thorough structure–activity-relationship as well as mode-of-action studies in the near future.

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