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Table 3 Comparison of two methods in the production of chiral glycidol derivatives

From: Asymmetric bio-epoxidation catalyzed with the styrene monooxygenase from Pseudomonas sp. LQ26

Entry R= Method 1a Method 2a
Yield (%)b ee (%) dr Yield (%)b ee (%) dr
1 Ph 50 >99 98:2 >99 >99 >99:1
2 m-FC6H4 51 >99 96:4 97 >99 >99:1
3 p-FC6H4 50 >99 96:4 98 >99 >99:1
4 m-ClC6H4 42 97 89:11 83 >99 >99:1
5 p-ClC6H4 46 >99 >99:1 84 >99 >99:1
6 m-BrC6H4 28 92 87:13 54 >99 >99:1
7 p-BrC6H4 35 >99 >99:1 64 >99 >99:1
8 m-MeC6H4 48 >99 98:2 87 >99 >99:1
9 p-MeC6H4 50 98 >99:1 86 >99 >99:1
10 m-OMeC6H4 17 >99 92:8 37 >99 >99:1
11 p-OMeC6H4 17 >99 98:2 75 >99 >99:1
12 2-thienyl 58 98 62:38 79 >99 96:4
13 3-thienyl 40 >99 92:8 98 >99 >99:1
14 benzyl 25 >99 86:14 55 >99 >99:1
  1. aThe schemes for Methods 1 and 2 are shown in Fig. 3. Briefly, Method 1 uses racemic allylic alcohols as the substrates and recombinant E. coli BL21 cells expressing SMO as the catalyst, and the reactions continue for 2–48 h at 30 °C. Method 2 uses α,β-unsaturated ketones as the substrates. The bioreduction of ketones was first performed in the presence of both ChKRED03 and the GDH/glucose system. Then freshly harvested whole cells of recombinant E. coli expression SMO were added, and the incubation was continued at 30 °C for 2–36 h
  2. bDetermined via reverse-phase HPLC analysis, and defined as (moles of product formed)/(moles of total added substrate)