Depurination | R.T. (min) | Relative Amount of Products | ||||||||
---|---|---|---|---|---|---|---|---|---|---|
Compounds and Reactions | 0.25 h | 0.5 h | 1 h | 2 h | 4 h | 8 h | 24 h | |||
Formic acid | 5 | 11.9 | 1.0 | 0.57 | 0.44 | 0.41 | 0.36 | 0.41 | 0.25 | |
5a/5b | Mono-spirocyclization | 10.5, 10.6 | 0.45 | 0.20 | 0.13 | 0.12 | 0.12 | 0.29 | 0.23 | |
5c | Di-spirocyclization | 9.1 | 0.20 | 0.09 | 0.06 | 0.05 | 0.05 | 0.17 | 0.15 | |
5d/5e | Mono-adenine alkylation | 9.7 | 0.14 | 0.27 | 0.28 | 0.41 | 0.47 | 0.65 | 0.88 | |
5f/5g | Adenine alkylation and spirocyclization | 8.5 | 0 | 0 | 0 | 0 | 0.01 | 0.01 | 0.02 | |
5h/5i | Adenine alkylation and hydroxylation | 8.3 | 0.01 | 0.03 | 0.03 | 0.05 | 0.06 | 0.08 | 0.15 | |
5j | Di-adenine alkylation | 8 | 0 | 0 | 0 | 0.02 | 0.04 | 0.07 | 0.15 | |
Heating | 5 | 11.9 | 0.13 | 0.27 | 0.23 | 0.31 | 0.33 | 0.16 | 0.04 | |
5a/5b | Mono-spirocyclization | 10.5, 10.6 | 0.09 | 0.51 | 0.27 | 0.57 | 0.81 | 0.07 | 0.01 | |
5c | Di-spirocyclization | 9.1 | 0.34 | 1.05 | 0.58 | 1.49 | 1.75 | 0.30 | 0.04 | |
5d/5e | Mono-adenine alkylation | 9.7 | 0 | 0 | 0 | 0.02 | 0.01 | 0.01 | 0 | |
5f/5g | Adenine alkylation and spirocyclization | 8.5 | 0.09 | 0.14 | 0.22 | 0.30 | 0.23 | 0.30 | 0.16 | |
5h/5i | Adenine alkylation and hydroxylation | 8.3 | 0.02 | 0.03 | 0.06 | 0.11 | 0.09 | 0.14 | 0.11 | |
5j | Di-adenine alkylation | 8 | 0 | 0.07 | 0.14 | 0.27 | 0.26 | 0.88 | 0.66 |
R.T., retention time.