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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)