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

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.

SUBMITTER: Yim VV

PROVIDER: S-EPMC7417771 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Thiol-ene Enabled Chemical Synthesis of Truncated <i>S</i>-Lipidated Teixobactin Analogs.

Yim Victor V VV Cameron Alan J AJ Kavianinia Iman I Harris Paul W R PWR Brimble Margaret A MA

Frontiers in chemistry 20200804

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 <i>S</i>-lipidated cyclic lipopeptides. ...[more]

PMID: 32850619

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