Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

Rebecca R. Midtkandal, Philip Redpath, Samuel A. J. Trammell, Simon J. F. Macdonald, Charles Brenner, Marie E. Migaud

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed. (c) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)5204-5207
Number of pages4
JournalBioorganic & Medicinal Chemistry Letters
Volume22
Issue number16
DOIs
Publication statusPublished - 15 Aug 2012

Keywords

  • C-Nucleoside
  • Benzamide riboside
  • Intramolecular cyclisation
  • Inosine monophosphate dehydrogenase
  • Nicotinamide adenine dinucleotide

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Midtkandal, R. R., Redpath, P., Trammell, S. A. J., Macdonald, S. J. F., Brenner, C., & Migaud, M. E. (2012). Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside. Bioorganic & Medicinal Chemistry Letters, 22(16), 5204-5207. https://doi.org/10.1016/j.bmcl.2012.06.069