Table 2.
Biocatalytic conversion of substrates 5‐Cl and 5‐Br.
| Entry | Enzyme | X | Conv. [%][a] | Selectivity [red/c] |
de trans/cis
[%][b] |
ee [%][b]
(S,S)‐7 |
ee [%][b]
(R,S)‐7 |
|---|---|---|---|---|---|---|---|
| 1 | WT OPR3 | Cl | >99 | 57:43 | 68 | 87 | >99 |
| 2 | OPR3 Y190F | Cl | >99 | 19:81 | 57 | 61 | 54 |
| 3 | OPR3 Y190W | Cl | >99 | 22:78 | 64 | 31 | 24 |
| 4 | WT YqjM | Cl | 95 | 69:31 | 67 | 52 | 56 |
| 5 | YqjM Y169F | Cl | >99 | 12:88 | 72 | −80 | −55 |
| 6 | WT OPR3 | Br | >99 | 13:87 | 14 | 92 | n.d. |
| 7 | OPR3 Y190F | Br | >99 | 1:99 | 58 | 22 | n.d. |
| 8 | OPR3 Y190W | Br | 70 | 1:99 | 13 | 39 | n.d. |
| 9 | WT YqjM | Br | >99 | 35:65 | −54 | 81 | n.d. |
| 10 | YqjM Y169F | Br | >99 | 1:99 | −30 | −67 | n.d. |
[a] Conversions were determined by GC‐FID analysis of the crude reaction mixture by using 1,2‐DME as an internal standard; n.d.=not detected. [b] For assignment of de and ee products were analyzed as the corresponding alcohols after reduction of the samples using NaBH4.