ArticleACS omega2020
Solid-Phase Synthesis of Biaryl Cyclic Lipopeptides Derived from Arylomycins.
Article in ACS omega, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Applications of biaryl cyclization in the synthesis of cyclic enkephalin analogs with a highly restricted flexibility.Amino acids · 2024Article
- Nitrilium ion trapping as a strategy to access structurally diverse heterobiaryl-containing peptide macrocycles.Chemical science · 2023Article
- Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles.Molecules (Basel, Switzerland) · 2022Review
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Authors and funding
5 authors.
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Abstract
An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe-Tyr, a Tyr-Tyr, or a His-Tyr linkage. This methodology first involved an intramolecular Suzuki-Miyaura arylation of a linear peptidyl resin incorporating the corresponding halogenated amino acid at the N-terminus and a boronotyrosine at the C-terminus. After N-methylation of the resulting biaryl cyclic peptidyl resin, the N-methylated lipopeptidyl tail was then assembled. The biaryl cyclic lipopeptides were purified and characterized.
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