Synthesis of orthogonally protected 1,2-diaminopropanoic acids by ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine: a study of the regioselectivity of the reaction

O’Brien, Keith; Kelleher, Fintan

doi:10.1016/j.tetlet.2013.09.116

Cited by 8 publications

(1 citation statement)

References 39 publications

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“…Numerous methods exist for the preparation of monoalkylated mDap but have drawbacks with the scalability and stereospecificity of required laborious purification steps. , Some methods, while being more applicable, limit the choice of protective groups, which are not consistent with our strategy for the final product synthesis . The suitable precursor was identified as Cbz- l -Dap-OH, which can be prepared from commercially available Cbz- l -Asn-OH 5 in large quantities via a Hoffmann degradation using PhI(OAc) 2 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%