Table 1.
Substrate scope of the epoxidation of styrene derivatives with immobilised rAaeUPO. Data are an average of duplicates and corrected from potential substrate evaporation.[a]
|
| ||||||
|---|---|---|---|---|---|---|
|
Substrate |
Epoxy product [mM] |
ee [%] |
Carbonyl product[b] [mM(%)] |
Time [h] |
TON[c] |
|
|
|
1 a |
16 |
12 |
2 (12) |
42 |
3203 |
|
|
2 a |
80 |
30 |
47 (37) |
86 |
22598 |
|
|
3 a |
9 |
35 |
1 (11) |
86 |
1779 |
|
|
4 a |
36 |
>99 |
2 (4) |
21 |
6762 |
|
|
5 a |
59 |
9 |
21 (26) |
60 |
14235 |
|
|
6 a |
24 |
50 |
102 (81) |
62 |
22420 |
|
|
7 a |
10 |
39 |
90 (90) |
49 |
17794 |
|
|
8 a |
8 |
12 |
22 (73) |
62 |
5338 |
|
|
9 a |
16 |
17 |
12 (43) |
42 |
4982 |
|
|
10 a |
15 |
15 |
22 (59) |
22 |
6584 |
|
|
11 a |
11 |
15 |
25 (69) |
42 |
6406 |
|
|
12 a |
3 |
42 |
1 (23) |
42 |
712 |
|
|
13 a |
14 |
–[d] |
60 (81) |
62 |
13167 |
|
|
14 a |
36 |
28 |
59 (62) |
97 |
16904 |
|
|
15 a |
4 |
6 |
25 (86) |
49 |
5160 |
|
|
16 a |
none |
– |
– |
– |
0 |
|
|
17 a |
136 |
42 |
147 (52) |
108 |
50356 |
|
|
18 a |
none |
– |
33 (100) |
69 |
5872 |
[a] Reaction conditions: [rAaeUPO]=5.62 μM, tBuOOH dosing rate=5 mM/h, room temperature, 20 rpm in overhead rotator. [b] The concentrations of carbonyl product were calculated using the calibration curves of the epoxides. Carbonyl products are aldehyde or ketone in β position from the ring opening of the epoxides, [c] TON=[product]/[enzyme], [d] n.d.=not determined.