A natural protecting group strategy to carry an amino acid starter unit in the biosynthesis of macrolactam polyketide antibiotics

J Am Chem Soc. 2011 Nov 16;133(45):18134-7. doi: 10.1021/ja208927r. Epub 2011 Oct 25.

Abstract

Macrolactam antibiotics are an important class of macrocyclic polyketides that contain a unique nitrogen-containing starter unit. In the present study, a set of starter biosynthetic enzymes in the macrolactam antibiotic vicenistatin was characterized. We found that the protection-deprotection strategy of the aminoacyl-ACP intermediate was critical in this system. On the basis of bioinformatics, the described pathway is also proposed as a common method for carrying amino acids in the biosynthesis of other macrolactam antibiotics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Aminoglycosides / biosynthesis*
  • Aminoglycosides / chemistry
  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry
  • Carboxy-Lyases / chemistry
  • Carboxy-Lyases / metabolism*
  • Intramolecular Transferases / chemistry
  • Intramolecular Transferases / metabolism*
  • Lactams / chemistry
  • Ligases / chemistry
  • Ligases / metabolism*
  • Macrolides / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Amino Acids
  • Aminoglycosides
  • Anti-Bacterial Agents
  • Lactams
  • Macrolides
  • vicenistatin
  • Carboxy-Lyases
  • Intramolecular Transferases
  • methylaspartate mutase
  • Ligases