NosA catalyzing carboxyl-terminal amide formation in nosiheptide maturation via an enamine dealkylation on the serine-extended precursor peptide

J Am Chem Soc. 2010 Nov 24;132(46):16324-6. doi: 10.1021/ja106571g. Epub 2010 Nov 3.

Abstract

The carboxyl-terminal amide group has been often found in many bioactive peptide natural products, including nosiheptide belonging to the over 80 entity-containing thiopeptide family. Upon functional characterization of a novel protein NosA in nosiheptide biosynthesis, herein we report an unusual C-terminal amide forming strategy in general for maturating certain amide-terminated thiopeptides by processing their precursor peptides featuring a serine extension. NosA acts on an intermediate bearing a bis-dehydroalanine tail and catalyzes an enamide dealkylation to remove the acrylate unit originating from the extended serine residue.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Catalysis
  • Dealkylation
  • Molecular Sequence Data
  • Molecular Structure
  • Protein Precursors*
  • Serine / chemistry*
  • Streptomyces / enzymology
  • Thiazoles / chemistry

Substances

  • Protein Precursors
  • Thiazoles
  • Serine
  • nosiheptide