title: NMR conformational analysis of p-tolyl furanopyrimidine 2'-deoxyribonucleoside and crystal structure of its 3',5'-di-O-acetyl derivative.
abstract: The conformation of a representative molecule of a new, potent class of antiviral-active modified nucleosides is determined. A bicyclic nucleoside, 3-(2'-deoxy-beta-D-ribofuranosyl)-6-(4-methylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one, shows C2'-endo and C3'-endo ribose conformations in solution (63:37, 37 degrees C; DMSO-d6), as determined by 1H NMR studies. The crystal structure of a 3',5'-di-O-acetyl-protected derivative (monoclinic, P21, a/b/c= 6.666(1)/12.225(1)/24.676(2) A, beta=90.24(1) degrees , Z=4) shows exclusively C2'-endo deoxyribose puckering. The base is found in the anti position both in solution and in crystalline form.
authors.affiliation: Department of Chemistry and Center for Biomedical Research, Oakland University, 2200 N. Squirrel Rd, Rochester, MI 48309-4477, USA.
authors.forename: Noor
authors.initials: N
authors.lastname: Esho
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Desaulniers
authors.forename: Brian
authors.initials: B
authors.lastname: Davies
authors.forename: Helen M-P
authors.initials: HM
authors.lastname: Chui
authors.forename: Meneni Srinivasa
authors.initials: MS
authors.lastname: Rao
authors.forename: Christine S
authors.initials: CS
authors.lastname: Chow
authors.forename: Slawomir
authors.initials: S
authors.lastname: Szafert
authors.forename: Roman
authors.initials: R
authors.lastname: Dembinski
mesh_terms: D018360:Crystallography, X-Ray; D003853:Deoxyribonucleosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D003853:Deoxyribonucleosides; D011743:Pyrimidines; C502479:p-tolyl furanopyrimidine 2'-deoxyribonucleoside