Preparation of potential cell-permeant nucleoside-2',3'-cyclic phosphate precursors.
Uridine-3'-phosphorothiolate triesters bearing lipophilic moieties were prepared via Michaelis-Arbuzov chemistry. Subsequent deprotection of the S-cholesteryl phosphorothiolate triester afforded the corresponding diester which underwent spontaneous Cyclization to cleanly afford uridine 2',3'-cyclic phosphate. This transesterification reaction could be expedited by treatment with iodine under mild, neutral conditions.
Battaggia
Simone
S
School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, United Kingdom.
Smith
Emma E
EE
Vyle
Joseph S
JS
D001921:Brain / Q000378:metabolism; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D004220:Disulfides / Q000737:chemistry; D011992:Endosomes / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009135:Muscular Diseases / Q000188:drug therapy; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D020033:Protein Isoforms; D014529:Uridine / Q000737:chemistry
D004220:Disulfides; D009705:Nucleosides; D009711:Nucleotides; D004364:Pharmaceutical Preparations; D010710:Phosphates; D020033:Protein Isoforms; D014529:Uridine