NMR conformational analysis of p-tolyl furanopyrimidine 2'-deoxyribonucleoside and crystal structure of its 3',5'-di-O-acetyl derivative.
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.
Esho
Noor
N
Department of Chemistry and Center for Biomedical Research, Oakland University, 2200 N. Squirrel Rd, Rochester, MI 48309-4477, USA.
Desaulniers
Jean-Paul
JP
Davies
Brian
B
Chui
Helen M-P
HM
Rao
Meneni Srinivasa
MS
Chow
Christine S
CS
Szafert
Slawomir
S
Dembinski
Roman
R
D018360:Crystallography, X-Ray; D003853:Deoxyribonucleosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D003853:Deoxyribonucleosides; D011743:Pyrimidines; C502479:p-tolyl furanopyrimidine 2'-deoxyribonucleoside