Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

Org Biomol Chem. 2014 Jun 21;12(23):3813-5. doi: 10.1039/c4ob00705k.

Abstract

We describe a practical, large-scale synthesis of the "fairy-ring" plant-growth regulator 2-azahypoxanthine (AHX), and its biologically active hydroxyl metabolite (AOH) and riboside derivative (AHXr). AHXr, a biosynthetic intermediate, was synthesized from inosine via a biomimetic route. Biotinylated derivatives of AHX and AHXr were also synthesized as probes for mechanistic studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Biotin / chemistry*
  • Chemistry, Organic / methods*
  • Hypoxanthines / chemical synthesis*
  • Hypoxanthines / chemistry
  • Plant Growth Regulators / chemical synthesis*
  • Plant Growth Regulators / chemistry
  • Staining and Labeling*

Substances

  • Alkynes
  • Azides
  • Hypoxanthines
  • Plant Growth Regulators
  • Biotin
  • 2-azahypoxanthine