4.8 Article

Synthesis and Biological Activity of Oxa-Lacticin A2, a Lantibiotic Analogue with Sulfur Replaced by Oxygen

Journal

ORGANIC LETTERS
Volume 11, Issue 24, Pages 5574-5577

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9025205

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Funding

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)
  2. Canada Research Chair
  3. Alberta Heritage Foundation for Medical Research (AHFMR)

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An oxidatively stable analogue 3 of lacticin 3147 A2 (2), wherein the sulfur atoms are replaced with oxygens, was synthesized using solution phase peptide synthesis and sequential on-resin cyclizations. Biological evaluation suggests that oxa-lacticin A2 (3) retains independent antimicrobial activity against Gram-positive bacteria but lacks the synergistic activity with natural lacticin A1 that is characteristic of the native lacticin A2 peptide.

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