Synthesis of Unnatural 2-Substituted Quinolones and 1,3-Diketones by a Member of Type III Polyketide Synthases from Huperzia serrata

Org Lett. 2016 Aug 5;18(15):3550-3. doi: 10.1021/acs.orglett.6b01501. Epub 2016 Jul 11.

Abstract

A curcuminoids, benzalacetone-, and quinolone-producing type III polyketide synthase (HsPKS3) from Huperzia serrata uniquely catalyzes the formation of unnatural 2-substituted quinolones and 1,3-diketones via head-to-head condensation of two completely different substrates. The broad range of substrate tolerance of HsPKS3 facilitates accessing structurally diverse 2-substituted quinolones and 1,3-diketones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Cyclization
  • Huperzia / enzymology
  • Ketones / chemical synthesis*
  • Ketones / isolation & purification
  • Plant Proteins / chemistry*
  • Polyketide Synthases / chemistry*
  • Quinolones / chemical synthesis*
  • Quinolones / isolation & purification

Substances

  • Ketones
  • Plant Proteins
  • Quinolones
  • Polyketide Synthases