Synthesis and biological activity of oxa-lacticin A2, a lantibiotic analogue with sulfur replaced by oxygen.
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.
Liu
Hongqiang
H
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Pattabiraman
Vijaya R
VR
Vederas
John C
JC
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001430:Bacteriocins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects; D013294:Lactococcus lactis / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D010100:Oxygen / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D001430:Bacteriocins; C546651:oxa-lacticin A2; C082508:lacticin 481; D013455:Sulfur; D010100:Oxygen