Synthesis of nucleoside analogues bearing the five naturally occurring nucleic acid bases built on a 2-oxabicylo[3.1.0]hexane scaffold.
Hitherto unknown nucleoside analogues incorporating the five naturally occurring nucleic acid bases built on a 2-oxabicyclo[3.1.0]hexane template were synthesized. The synthesis of these new conformationally restricted nucleoside analogues involved the preparation of a suitable sugar precursor bearing the 2-oxabicyclo[3.1.0]hexane scaffold. This sugar was readily obtained from [(3aS,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzyl ether (4) following a Simons-Smith-type cyclopropanation reaction. Finally, glycosylation reactions and deprotection provided the nucleoside analogues. Using nucleoside 14 bearing thymine base as a model, we found that the conformation of such nucleoside analogue was restricted toward a (0)T(1) conformation.
Gagneron
Julien
J
Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-Université Montpellier II, case courrier 008, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France.
Gosselin
Gilles
G
Mathé
Christophe
C
D006586:Hexanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009696:Nucleic Acids / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006586:Hexanes; D009696:Nucleic Acids; D009705:Nucleosides