Synthesis of Cytokinins via Enzymatic Arsenolysis of Purine Nucleosides

Curr Protoc Nucleic Acid Chem. 2018 Dec;75(1):e61. doi: 10.1002/cpnc.61. Epub 2018 Oct 9.

Abstract

This unit describes an effective method for the preparation of natural cytokinins and their synthetic derivatives based on enzymatic cleavage of the N-glycosidic bond of N6 -substituted adenosine or O6 -substituted inosine derivatives in the presence of purine nucleoside phosphorylase (PNP) and Na2 HAsO4 . The arsenolysis reaction is irreversible due to the hydrolysis of the resulting α-D-ribose-1-arsenate. As a result, the desired products are formed in near-quantitative yields, as indicated by high-performance liquid chromatography (HPLC) analysis, and can easily be isolated. In the strategy used here, the ribose residue acts as a protective group. © 2018 by John Wiley & Sons, Inc.

Keywords: adenine derivatives; cytokinins; enzymatic arsenolysis; hypoxanthine derivatives; purine nucleoside phosphorylase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arsenates / chemistry*
  • Chromatography, High Pressure Liquid
  • Cytokinins / chemical synthesis*
  • Cytokinins / chemistry
  • Cytokinins / isolation & purification
  • Mass Spectrometry
  • Proton Magnetic Resonance Spectroscopy
  • Purine Nucleosides / metabolism*
  • Purine-Nucleoside Phosphorylase / metabolism*

Substances

  • Arsenates
  • Cytokinins
  • Purine Nucleosides
  • Purine-Nucleoside Phosphorylase
  • arsenic acid