Assessing oxazole bioisosteres as mutasynthons on the rhizoxin assembly line

Chembiochem. 2011 Oct 17;12(15):2284-8. doi: 10.1002/cbic.201100387.

Abstract

Chain armor against tumor cells: The oxazole side chain in the antimitotic agent rhizoxin S2 (1) was successfully replaced through mutasynthesis by using an engineered mutant impaired in heterocyclization. Incorporation of 12 non-natural surrogates into fully processed rhizoxin analogues revealed a remarkable substrate flexibility of the PKS-NRPS hybrid.

MeSH terms

  • Amino Acid Sequence
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / metabolism*
  • Burkholderia / chemistry
  • Burkholderia / enzymology*
  • Burkholderia / genetics*
  • Burkholderia / metabolism
  • Genes, Fungal
  • Genetic Loci
  • Macrolides / chemistry
  • Macrolides / metabolism*
  • Molecular Sequence Data
  • Mutation
  • Oxazoles / chemistry
  • Oxazoles / metabolism*
  • Peptide Synthases / genetics
  • Peptide Synthases / metabolism
  • Polyketide Synthases / genetics
  • Polyketide Synthases / metabolism

Substances

  • Antibiotics, Antineoplastic
  • Macrolides
  • Oxazoles
  • Polyketide Synthases
  • rhizoxin
  • Peptide Synthases