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. Author manuscript; available in PMC: 2010 Apr 14.
Published in final edited form as: Adv Synth Catal. 2009 Nov;351(17):2976–2990. doi: 10.1002/adsc.200900603

Table 6.

The effect of time on the reduction of ketoisophorone 3a and product racemisation catalysed by PETNR (0.02 μM).[a]

Entry Time [h] Conv.[b] [%] Yield[b] [%] ee[c] [%]
1 0.5 14 12 >99
2 1 27 23 99
3 1.5 37 35 98
4 3 53 53 93
5 4 69 65 90
6 6 85 80 82
7 8 94 87 76
8 12 98 88 69
9 22 >99 91 33
10 24 >99 95 30
11 24[d] 99 nd 30
12 24[e] 99 nd 29
[a]

Conditions: alkene 3a (5 mM), PETNR (0.02 μM), NADPH (6 mM) in phosphate buffer (50 mM, pH 7.0, 1 mL total volume), 30 °C at 130 rpm, 2 h. Alkene 3a was added as a DMF solution (2% final DMF solution).

[b]

By GC using a DB-Wax column.

[c]

By GC using a Chirasil-DEX-CB column.

[d]

Filtered using 10 K millipore filter after 8 h to remove all enzyme content.

[e]

PETNR inhibitor NADPH4 (1.2 mg) added after 8 h to inhibit enzymatic activity.