Biocatalytic separation of N-7/N-9 guanine nucleosides

J Org Chem. 2010 Nov 19;75(22):7932-5. doi: 10.1021/jo101565e. Epub 2010 Oct 25.

Abstract

Vorbrüggen coupling of trimethylsilylated 2-N-isobutanoylguanine with peracetylated pentofuranose derivatives generally gives inseparable N-7/N-9 glycosyl mixtures. We have shown that the two isomers can be separated biocatalytically by Novozyme-435-mediated selective deacetylation of the 5'-O-acetyl group of peracetylated N-9 guanine nucleosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Enzymes, Immobilized
  • Fungal Proteins
  • Guanine / analogs & derivatives*
  • Guanine / chemistry*
  • Isomerism
  • Lipase / chemistry*
  • Magnetic Resonance Spectroscopy
  • Nucleosides / chemistry*
  • Purine Nucleosides / chemistry*

Substances

  • Enzymes, Immobilized
  • Fungal Proteins
  • Nucleosides
  • Purine Nucleosides
  • Guanine
  • Novozyme 435
  • Lipase