858669-63-3Relevant academic research and scientific papers
Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin
Mukherjee, Subha,Huo, Liujie,Thibodeaux, Gabrielle N.,Van Der Donk, Wilfred A.
, p. 6188 - 6191 (2016/12/09)
Cytolysin, a two-component lanthipeptide comprising cytolysin S (CylLS″) and cytolysin L (CylLL″), is the only family member to exhibit lytic activity against mammalian cells in addition to synergistic antimicrobial activity. A subset of the thioether cross-links of CylLS″ and CylLL″ have ll stereochemistry instead of the canonical dl stereochemistry in all previously characterized lanthipeptides. The synthesis of a CylLS″ variant with dl stereochemistry is reported. Its antimicrobial activity was found to be decreased, but not its lytic activity against red blood cells. Hence, the unusual ll stereochemistry is not responsible for the lytic activity.
Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry
Knerr, Patrick J.,Van Der Donk, Wilfred A.
, p. 7094 - 7097 (2013/06/27)
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 stereoche
Chemical synthesis and biological activity of analogues of the lantibiotic epilancin 15X
Knerr, Patrick J.,Van Der Donk, Wilfred A.
, p. 7648 - 7651 (2012/06/18)
Lantibiotics are a large family of antibacterial peptide natural products containing multiple post-translational modifications, including the thioether structures lanthionine and methyllanthionine. Efforts to probe structure-activity relationships and engineer improved pharmacological properties have driven the development of new methods to produce non-natural analogues of these compounds. In this study, solid-supported chemical synthesis was used to produce analogues of the potent lantibiotic epilancin 15X, in order to assess the importance of several N-terminal post-translational modifications for biological activity. Surprisingly, substitution of these moieties, including the unusual N-terminal d-lactyl moiety, resulted in relatively small changes in the antimicrobial activity and pore-forming ability of the peptides.
Versatile and stereoselective syntheses of orthogonally protected β-methylcysteine and β-methyllanthionine
Narayan, Radha S.,VanNieuwenhze, Michael S.
, p. 2655 - 2658 (2007/10/03)
(Chemical Equation Presented) Lantibiotics are a class of lanthionine (and/or β-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic s
