Compound 11
N 6-methyladenosine
From: Mycobacterium tuberculosis releases an antacid that remodels phagosomes
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- (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
General procedure for preparation of the N6-adenosine analogues: To a flask containing 1-alkylated adenosine (0.35 mmol) was added an 11 M solution of dimethylamine (1.8 mL). The resulting transparent reaction mixture was stirred overnight after which TLC showed complete conversion. The solvent was removed by a rotary evaporation under reduced pressure. All products were obtained quantitatively. Following the general procedure outlined above the product was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 2H), 8.21 (s, 1H), 7.77 (s, 1H), 5.88 (d, J = 6.2 Hz, 1H), 5.44 (s, 1H), 5.20 (s, 1H), 4.60 (dt, J = 7.2, 4.1 Hz, 1H), 4.15 (t, J = 3.8 Hz, 1H), 3.97 (q, J = 3.4 Hz, 1H), 3.66 (dd, J = 12.1, 3.6 Hz, 1H), 3.55 (dd, J = 12.2, 3.6 Hz, 1H), 2.94 (s, 3H). 13C NMR (101 MHz, DMSO-d6) δ 155.11, 152.46, 148.07, 139.72, 119.88, 87.96, 85.97, 73.53, 70.70, 61.72, 27.09. HRMS (ESI+, m/z): calculated for C11H16N5O4 [M+H]+: 282.1197; found: 282.1198. The obtained 1H NMR and 13C NMR spectra contained an additional signal at 2.54 ppm (1H) and 34.29 ppm (13C) respectively, which corresponds to residual dimethyl ammonium salts. The NMR spectra are in agreement with previously reported data: K. Tatani, M. Hiratochi, Y. Nonaka, M. Isaji, and S. Shuto. ACS Med. Chem. Lett. 2015, 6, 244-248.
