Table 2.
Reduction of various activated alkenes by PETNR using NADP+/G6PDH co-factor regeneration system.[a]
| Entry | Substrate | Conf. | Product | t [h] | Conv.[b] [%] | Yield[b] [%] | ee[c] [%] | |
|---|---|---|---|---|---|---|---|---|
| 1 | 1a |
|
(R)-1b |
|
24 | >99 | 98 | >99 |
| 2 | 2a |
|
(R)-2b |
|
24 | >99 | 99 | >99 |
| 3 | 3a |
|
(R)-3b |
|
24 | >99 | 95 | 49 |
| 4 | 5a |
|
(R)-5b |
|
24 | >99 | 93 | 98 |
| 5 | (5R)-6a |
|
(2R,5R)-6b |
|
24 | >99 | 82 | 95%[d,e] |
| 6 | (5S)-7a |
|
(2R, 5S)-7b |
|
24 | >99 | 95 | 88%[d,e] |
| 7 | 10a |
|
(S)-10b |
|
24 | >99 | 85 | 66 |
| 8 | 11a |
|
(S)-11b |
|
24 | >99 | 56 | 87 |
| 9 | 15a |
|
(S)-15b |
|
24 | 25 | 18 | >99 |
| 10 | 16a |
|
(S)-16b |
|
24 | 14 | 14 | >99 |
| 11 | 17a |
|
(S)-17b |
|
24 | 58 | 56 | 70 |
| 12 | (E)-18a |
|
(S)-18b |
|
24 | 96 | 70 | 69 |
| 13 | (Z)-18a |
|
(S)-18b |
|
24 | >99 | 87 | 95 |
| 14 | (E)-19a |
|
(S)-19b |
|
24 | 64 | 40 | 64 |
Conditions: Reactions contained potassium phosphate buffer (50 mM KH2PO4/K2HPO4 pH 7.0, 1.0 mL), alkene (5 mM), PETN reductase (2 μM), glucose 6-phosphate dehydrogenase (10 U), glucose 6-phosphate (15 mM) and NADP+ (10 μM). Reactions were agitated at 30 °C at 130 rpm for 24 h. Alkenes 1a, 3a and 18-19a were added as a DMF solution [2% (v/v) final DMF concentration].
by GC using DB-Wax column.
By GC or HPLC.