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Thiol-ene Enabled Chemical Synthesis of Truncated S-Lipidated Teixobactin Analogs

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Herein is described the introduction of lipid moieties onto a simplified teixobactin pharmacophore using a modified Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technique, whereby cysteine was substituted… Click to show full abstract

Herein is described the introduction of lipid moieties onto a simplified teixobactin pharmacophore using a modified Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technique, whereby cysteine was substituted for 3-mercaptopropionic acid (3-MPA). A truncated teixobactin analog was prepared with the requisite thiol handle, thus enabling an array of vinyl esters to be conveniently conjugated onto the simplified teixobactin pharmacophore to yield S-lipidated cyclic lipopeptides.

Keywords: enabled chemical; teixobactin; thiol ene; chemical synthesis; synthesis truncated; ene enabled

Journal Title: Frontiers in Chemistry
Year Published: 2020

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