Unusual entry to the novel 8-halo-N1-ribosyl hypoxanthine system by degradation of a cyclic adenosine-5'-diphosphate ribose analogue

Chem Commun (Camb). 2006 Mar 14:(10):1127-9. doi: 10.1039/b517916e. Epub 2006 Jan 25.

Abstract

Cyclic 8-bromo-inosine-5'-diphosphate ribose (8-Br-N1-cIDPR) was cleanly degraded at acidic pH by N9 ribosyl scission and subsequent pyrophosphate cleavage to give 8-bromo-N1-ribosyl hypoxanthine 5'-monophosphate (8-Br-N1-IMP), a novel class of mononucleotide, as the sole product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclic ADP-Ribose / analogs & derivatives*
  • Cyclic ADP-Ribose / chemistry*
  • Hypoxanthine / chemistry*
  • Lactones / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Phosphates / chemistry*
  • Stereoisomerism

Substances

  • Lactones
  • Phosphates
  • Cyclic ADP-Ribose
  • Hypoxanthine