Table 2.
Chemoselectivity of myoglobin and other hemoproteins in the reaction with 4-(dimethylsilyl)styrene (3a) or para-amino-styrene (4a) and EDA.a
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Entry | Catalyst | % yield (3b+3c)b |
3b:3c ratio |
% yield (4b+4c) b |
4b:4c ratio |
1 | Mb | 6 | 3:97 | 65 | 1:99 |
2 | Mb(H64V,V68A) | 13 | 4:96 | 85 | 0:100 |
3 | HRP | 1 | 11:89 | 96 | 0:100 |
4 | Catalase | 1 | 9:91 | 6 | 2:98 |
5 | P450BM3 | <0.5 | 5:95 | 24 | 1:99 |
6 | FL#62 | 4 | 5:95 | 25 | 1:99 |
7 | cytochrome c | 10 | 5:95 | 57 | 1:99 |
Reaction conditions: 10 mM 3a or 4a, 10 mM EDA, 10 mM Na2S2O4, 20 μM catalyst in 50 mM phosphate buffer (pH 7.0).
Based on GC conversion using calibration curves with isolated 3b, 3c, 4b, and 4c.