Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry.

ABSTRACT: Lantibiotics are a family of antibacterial peptide natural products characterized by the post-translational installation of the thioether-containing amino acids lanthionine and methyllanthionine. Until recently, only a single naturally occurring stereochemical configuration for each of these cross-links was known. The discovery of lantibiotics with alternative lanthionine and methyllanthionine stereochemistry has prompted an investigation of its importance to biological activity. Here, solid-supported chemical synthesis enabled the total synthesis of the lantibiotic lacticin 481 and analogues containing cross-links with non-native stereochemical configurations. Biological evaluation revealed that these alterations abolished the antibacterial activity in all of the analogues, revealing the

SUBMITTER: Knerr PJ 

PROVIDER: S-EPMC3736828 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature