Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 2, Pages 462-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9095945
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Alberta Heritage Foundation for Medical Research (AHFMR)
- Canada Research Chair in Bioorganic and Medicinal Chemistry
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Lactocin S is a lantibiotic peptide with potent antibacterial activity against a range of Gram-positive bacteria. Because of challenges in obtaining sufficient quantities of this compound from natural Sources, the stereochemistry of the lanthionine residues in lactocin S had not been confirmed. This report describes the chemical synthesis of lactocin S on chlorotrityl polystyrene resin in 10% overall yield using intramolecular cyclization to form the lanthionine rings and employing fragment coupling for the two N-terminal residues. This represents the first report of solid-supported synthesis of a naturally occurring lantibiotic. Comparison to lactocin S isolated from Lactobacillus sakei L45 using a combination of HPLC, MS/MS sequencing, bacteria] testing, and chiral GC-MS analysis confirmed the initially proposed structure and the stereochemistry of the dl-lanthionine residues.
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