Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks.

Journal Article (Journal Article)

Nitrogen heterocycles are the key functional and structural elements in both RNA and DNA, in half a dozen of the most important coenzymes, and in many synthetic drug scaffolds. On the other hand, only 3 of 20 proteinogenic amino acids have nitrogen heterocycles: proline, histidine, and tryptophan. This inventory can be augmented in microbial proteins by posttranslational modifications downstream of leader peptide regions that convert up to 10 serine, threonine, and cysteine residues, side chains and peptide backbones, into oxazoles, thiazoles, and pyridine rings. Subsequent proteolysis releases these heterocyclic scaffolds in both linear and macrocyclic frameworks as bioactive small molecules.

Full Text

Duke Authors

Cited Authors

  • Walsh, CT; Malcolmson, SJ; Young, TS

Published Date

  • March 2012

Published In

Volume / Issue

  • 7 / 3

Start / End Page

  • 429 - 442

PubMed ID

  • 22206579

Pubmed Central ID

  • PMC3306484

Electronic International Standard Serial Number (EISSN)

  • 1554-8937

International Standard Serial Number (ISSN)

  • 1554-8929

Digital Object Identifier (DOI)

  • 10.1021/cb200518n


  • eng