Skip to main content
. Author manuscript; available in PMC: 2019 Jul 20.
Published in final edited form as: J Org Chem. 2018 Jul 6;83(14):7480–7490. doi: 10.1021/acs.joc.8b00946

Table 2.

Chemoselectivity of myoglobin and other hemoproteins in the reaction with 4-(dimethylsilyl)styrene (3a) or para-amino-styrene (4a) and EDA.a

graphic file with name nihms-997296-t0006.jpg
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
a

Reaction conditions: 10 mM 3a or 4a, 10 mM EDA, 10 mM Na2S2O4, 20 μM catalyst in 50 mM phosphate buffer (pH 7.0).

b

Based on GC conversion using calibration curves with isolated 3b, 3c, 4b, and 4c.