Chemical and Enzymatic Synthesis of 2′-Deoxy-iso-inosine and Its Incorporation into DNA

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• 1 : UV (H2O) λmax = 314 nm (3700). MS (CI, NH3) m/z 253 (M+H). HPLC (C18, 0 to 15% CH3CN in 10mM TEAA over 20 min. at a flow rate of 5.5 min.) Rt = 10.3 min. 1H NMR (D2O) δ : 2.20 (m, 1H, H2′); 2.72 (m, 1H, H2′); 3.74 (m, 2H, H5′ and H5′); 4.06 (m, 1H, H4′); 4.56 (m, 1H, H3′); 6.26 (t, 1H, H1′, J1,2′ = J1,2′ = 6.8 Hz); 8.32 (s, 1H, H8); 8.38 (s, 1H, H6). 13C NMR (D2O) δ : 39.16 (C2′); 62.18 (C5′); 71.73 (C3′); 84.62 (C1′); 87.98 (C4′); 124.96 (C5); 139.58 (C6); 147.67 (C8); 158.41 (C2); 159.28 (C4). Anal. Calcd for C10H12N4O4 (252.2 + 1.5 H2O): C, 43.00; H, 5.41; N, 20.06. Found: C, 43.15; H, 5.12; N, 20.45.
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