Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces isolate

Org Biomol Chem. 2015 Oct 7;13(37):9585-92. doi: 10.1039/c5ob01269d.

Abstract

Linaridins are rare linear ribosomally-synthesized and post-translationally modified peptides (RiPPs) and only two, cypemycin and SGR-1832, in this family have been identified so far. Legonaridin 1 has been discovered as a new member of linaridins through chemical isolation, peptidogenomics, comprehensive 1- and 2-D NMR and advanced Marfey's analyses from the soil bacterium Streptomyces sp. CT34, an isolate collected from Legon, Ghana. Bioinformatics analysis of the gene cluster suggested that the biosynthesis of legonaridin 1 is different from those of cypemycin and SGR-1832. Consistent with bioinformatics and peptidogenomics analyses, 1 has a total of nine post-modifications, 8 dehydrobutyrine residues and a N,N-dimethylated N-terminus with a carboxylic acid at the C-terminus. Legonaridin 1 is structurally different from the two known linaridins comprising a new subfamily. This is the first time that NMR spectroscopy is used to establish the 2-D structure of a linaridin RiPP.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Computational Biology
  • Data Mining
  • Molecular Sequence Data
  • Multigene Family
  • Peptides / chemistry*
  • Peptides / metabolism*
  • Protein Processing, Post-Translational*
  • Ribosomes / metabolism*
  • Streptomyces* / genetics
  • Streptomyces* / isolation & purification

Substances

  • Peptides