Table 1.
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Entry | Catalyst | [EDA] (mM) | Cell Density (gcdw/L) | [P450] (3M) | Yield (%) | TTN | cis:trans | eecis (%)* | eetrans (%)† |
1 | P450BM3-CIS | 8.5 | 7.7 | 3.7 | 42 | 950 | 22:78 | 60 | 22 |
2 | P411BM3-CIS | 8.5 | 7.7 | 1.3 | 55 | 3,700 | 76:24 | 96 | 25 |
3 | P411BM3-heme-CIS | 8.5 | 7.7 | 3.6 | 67 | 1,600 | 71:29 | 95 | 17 |
4 | P450BM3 | 8.5 | 13.4 | 4.8 | 0.9 | 15 | 25:75 | 24 | 21 |
5 | P411BM3 | 8.5 | 8.1 | 1.5 | 50 | 2,900 | 13:87 | 12 | 8 |
6 | P411BM3-CIS + CO | 8.5 | 8.4 | 1.8 | 0.6 | 30 | 20:80 | 35 | 20 |
7 | P411BM3-CIS‡ | 170 | 8.4 | 1.8 | 72 | 67,800 | 90:10 | 99 | 43 |
8 | P411BM3-CIS‡ | 200 | 20 | 3.2 | 78§ | 48,800 | 88:12 | 99 | 35 |
P411BM3 = P450BM3-C400S
TTN = total turnover number. Major products:
cis = (1R,2S);
trans = (1S,2S)
Neat reagents were used without addition of MeOH; reactions were left for 24 h.
Isolated yield (1.63 g cyclopropanes). The data represent the averages of triplicate experiments. Standard errors are within 20% of the reported average.