Jahnellamides, α-keto-β-methionine-containing peptides from the terrestrial myxobacterium Jahnella sp.: structure and biosynthesis

Org Lett. 2013 Nov 15;15(22):5882-5. doi: 10.1021/ol402967y. Epub 2013 Nov 7.

Abstract

Two new cyclic peptides, termed jahnellamides A and B, were isolated from the myxobacterium Jahnella sp. Their structures were solved by NMR, ESIMS, and chemical derivatizations. Jahnellamides are a new class of α-ketoamide-containing peptides comprised of nonproteinogenic amino acids, including α-keto-β-methionine and 4-hydroxyglutamic acid. Moreover, in silico analysis of the genome sequence along with feeding experiments allowed us to identify and annotate a candidate nonribosomal peptide synthetase biosynthetic gene cluster containing a polyketide synthase module involved in the formation of the α-ketoamide moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glutamates / chemistry*
  • Magnetic Resonance Spectroscopy
  • Methionine / chemistry*
  • Molecular Structure
  • Peptide Synthases / biosynthesis*
  • Peptide Synthases / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Peptides, Cyclic / biosynthesis*
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry*

Substances

  • Glutamates
  • Peptides
  • Peptides, Cyclic
  • jahnellamide A
  • jahnellamide B
  • hydroxyglutamic acid
  • Methionine
  • Peptide Synthases