Imidazole-4-Carboxamide and 1,2,4-Triazole-3-Carboxamide Deoxynucleotides as Simplified DNA Building Blocks with Ambiguous Pairing Capacity

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• NMR data: Compound 2: 1H NMR (D2O) δ: 2.60 (ddd, 1H, H2′); 2.85 (ddd, 1H, H2′); 3.70 (dd, 1H, H5′, J = 6.2 and J = 12.3); 3.80 (dd, 1H, H5′, J = 3.9 and J = 12.3); 4.15 (m, 1H, H4′); 4.65 (m, 1H, H3′); 6.41 (dd, 1H, HI', J = 5.1 and J = 6.7); 8.70 (s, 1H, H5). 13C NMR (D2O) δ: 39.69 (C21); 62.33 (C51); 71.47 (C31); 88.37 (C1′ ou C4′); 88.86 (C4′ ou Cl'); 146.57 (C5); 157.02 (C3); 163.72 (CONH2).Compound 4: 1H NMR (DMSO-d6) δ: 1.31 (t, 3H, CH3); 2.35 (m, 1H, H2′); 2.55 (m, 1H, H2′); 3.43 (m, 1H, H5′); 3.54 (m, 1H, H5′); 3.86 (m, 1H, H4′); 4.33 (q, 2H, CH2); 4.37 (m, 1H, H31); 4.88 (t, 1H, OH5′, J = 5.5); 5.35 (d, 1H, OH3′, J = 4.4); 6.28 (t, 1H, HI', J = 6); 8.90 (s, 1H, H5). 13C NMR (DMSO-d6) δ: 14.14 (CH3); 39.56 (C2′); 61.17 and 61.49 (CH2 and C5′); 70.09 (C31); 88.05 and 88.35 (Cl' and C4′); 145.29 (C5); 154.15 (C3); 159.48 (COOE8). Phosphoramidites: 31P NMR (CDCI3) δ: 147.10 and 147.18 ppm (7); 114.57, 114.64, 147.09, 147.17 (9); 147.14 and 146.03 ppm (8); 147.06and 147.01 ppm (13); 147.28 and 146.99 ppm (14).
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