10.1002/ejoc.201700466
European Journal of Organic Chemistry
FULL PAPER
in vacuo. The crude product was purified by flash column
chromatography using a hexanes/EtOAc (2:8) solvent system to
afford 0.173g (86%) of a colorless foam. Rf (SiO2 TLC): 0.11,
0.26 (1:1 hexanes/EtOAc). λmax(MeCN) = 283 nm. HRMS (ESI-MS)
m/z calculated for C40H49FN4O8P+: 763.3267; found 749.3104 [M
+ H]+. 1H NMR (500 MHz, CDCl3, ppm): 8.15-8.16 (d, J= 6.3 Hz,
0.5H; H6), 8.12-8.13 (d, J= 6.3 Hz, 0.5H; H6), 7.23–7.53 (m, 9H;
Ar), 6.89– 6.93 (m, 4H; Ar), 6.18-6.23 (m, 1H; H1’), 4.70-4.78 (m,
1H; H3’), 4.22-4.29 (m, 1H; H4’), 3.97-3.98 (s, 3H; OCH3), 3.63-
3.88 (m, 10H; NCH, ArOCH3, CH2OP), 3.43-3.52 (m, 2H; H5’,
H5’’), 2.77-2.80 (t, 1H; CH2CN), 2.60-2.70 (t, 1H; CH2CN), 2.39-
2.47 (m, 1H; H2’’), 2.06-2.07 (m, 1H; H2’’) 1.20-1.23 (m, 9H;
CH3), 1.12-1.14 (m, 3H; CH3). 13C NMR (125.7 MHz, CDCl3,
ppm): 205.21, 162.27, 162.17, 158.83, 152.36, 144.93, 137.15,
137.12, 135.62, 135.60, 135.51, 135.47, 135.21, 135.18, 130.11,
130.08, 128.06, 127.82, 127.81, 127.68, 127.65, 126.81, 126.79,
118.07, 117.94, 113.13, 113.11, 86.70, 86.65, 86.58, 86.51,
85.73, 85.70, 85.46, 85.41, 73.18, 73.05, 72.71, 72.58, 63.00,
62.80, 58.73, 58.67, 58.58, 58.52, 54.65, 54.63, 53.98, 43.13,
43.11, 43.03, 43.01, 40.36, 40.34, 40.17, 40.13, 29.42, 29.26,
29.11, 28.96, 28.80, 28.65, 19.90, 19.86, 19.84, 19.81. 19F
(470.4 MHz, d6-acetone, ppm): -171.63, -171.64, -171.68, -
171.70. 31P NMR (202.3 MHz, d6-acetone, ppm): 148.35, 148.21.
IR (thin film); νmax (cm−1) =3071, 2966, 2869, 2836, 2362, 2335,
2252, 1683, 1652, 1607, 1541, 1506, 1457, 1401, 1336, 1252,
1179, 1116, 1035, 977, 829, 734.
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Acknowledgements
We are grateful to Dr. Anthony E. Pegg (Pennsylvania State
University) for the plasmids encoding the wild-type hAGT, OGT
and Ada-C genes. We thank Drs. Derek O’Flaherty and Anne
Noronha for helpful discussions. This research was supported
by grants from the Natural Sciences and Engineering Research
Council of Canada (NSERC) and the Canada Foundation for
Innovation (CFI). L.S. is the recipient of a Bourse de maîtrise en
recherche from the Fonds de recherche du Québec - Nature et
technologies (FRQNT), a Concordia Graduate Scholarship in
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Keywords: O6-Alkylguanine DNA alkyltransferase, chemically
modified oligonucleotides, DNA repair, DNA damage, direct
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