Development of Novel Bridged and Caged Nucleoside Analogs as Biochemical Tools

Abstract

New classes of closely biomimetic, anti conformation restricted, transglycosidic spiro, bridged, and caged pyrimidine nucleoside analogs are being developed. Progress towards accessing members of the new caged 2′-deoxyuridine mimic class is related.

Notes

Characterization data for 5b: ¹H NMR ((CD₃),SO) δ 11.5 (1, br, NH), 6.37 (1, d, Hl′, ³ J _1′,2′., = 6.4 Hz), 5.83 and 5.77 (each 1, each s, H5 and H7), 5.71 (1, d, 3′-OH, ³ J3′-3′-OH = 4.3 Hz), 4.93 (1, d, H5′, ³ J4′-5′ = 3.8 Hz), 4.67 (1, d, H2′), 4.38 (1, d, H3′), 4.21 (1, d, H4′), 3.23 (3, s, CH₃O). ¹³C NMR ((CD₂SO) 162.4 (C4), 150.8 and 149.1 (C2/C6), 99.4 and 99.2 (C5′/C5), 88.0 (C7), 83.1 (C4′), 79.7 (C1′), 76.7 and 76.4 (C2′/C3′), 55.3 (CH₃O). LRFAB-MS, m/e 285.1 (40%, MH+). HRFAB-MS (C₃₃H₃₃N₄O₈): calcd 285.0723, found 285.0722.