Compound 5
1-phythyladenosinium
From: Mycobacterium tuberculosis releases an antacid that remodels phagosomes
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- 6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl)-9H-purin-1-ium
Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
The title compound was synthesised following the general procedure outlined for compound 8. A yellow solid (90% yield) was obtained after column chromatography using CH2Cl2: methanol (90:10) as the eluent. 1H NMR (400 MHz, CD3OD) δ 8.61 (s, 1H), 8.49 (s, 1H), 6.07 (d, J = 4.9 Hz, 2H), 5.45 (t, J = 6.9 Hz, 1H), 4.93 (d, J = 6.8 Hz, 2H), 4.66 – 4.52 (m, 1H), 4.35 (t, J = 4.7 Hz, 1H), 4.15 (q, J = 3.7 Hz, 1H), 3.86 (dd, J = 12.1, 4.2 Hz, 1H), 3.78 (dd, J = 12.1, 4.2 Hz, 1H), 2.13 (t, J = 7.7 Hz, 2H), 1.86 (s, 3H), 1.59 – 1.00 (m, 18H), 0.92 – 0.82 (m, 12H). 13C NMR (101 MHz, CD3OD) δ 152.43, 147.84, 147.70, 146.85, 143.95, 121.38, 116.03, 90.44, 87.46, 76.44, 71.82, 62.62, 49.40, 40.82, 40.48, 38.43, 38.38, 38.32, 37.73, 33.86, 33.77, 29.09, 26.10, 25.83, 25.44, 23.10, 23.01, 20.19, 20.11, 16.97. HRMS (ESI+, m/z): calculated for C30H52N5O4+: 546.4014; found: 546.4006.
