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Table 3 Enantioselective reaction of phenyl-ring-containing ketones and keto esters by SporeE228S-GDH in ethyl acetate solution

From: Efficient chiral synthesis by Saccharomyces cerevisiae spore encapsulation of Candida parapsilosis Glu228Ser/(S)-carbonyl reductase II and Bacillus sp. YX-1 glucose dehydrogenase in organic solvents

n

R1

R2

Abs.Config.a

Yield (%)

ee (%)

Time (h)

1

Ph

CH3

(R)-1b

88 (93)b

>99 (> 99)

4.5 (10)

2

Ph-p-CH3

CH3

(R)-2b

79 (89)

>99 (> 99)

4 (9)

3

Ph-p-OCH3

CH3

(R)-3b

45 (51)

>99 (> 99)

4 (10)

4

Ph-p-Br

CH3

(R)-7b

81 (90)

>99 (> 99)

4 (10)

5

Ph-p-Cl

CH3

(R)-6b

85 (93)

>99 (> 99)

4 (10)

6

Ph-o-Cl

CH3

(R)-4b

20 (17)

>99 (> 99)

4 (10)

7

Ph-m-Cl

CH3

(R)-5b

25 (28)

>99 (> 99)

4 (10)

8

Ph

CH2OH

(S)-8b

14 (13)

>99 (> 99)

4 (8)

9

CH3(CH2)2

CH3

(R)-9b

60 (34)

94 (86)

3 (8)

10

CH3(CH2)3

CH3

(R)-10b

56 (27)

91 (73)

3 (8)

11

CH3(CH2)4

CH3

(R)-11b

53 (22)

89 (68)

3 (8)

12

CH3(CH2)5

CH3

(R)-12b

43 (19)

85 (65)

3 (8)

13

CH3COO

O-CH3

(R)-13b

55 (35)

97 (83)

5 (12)

14

CCl3COCH2

O-CH2CH3

(R)-14b

52 (26)

90 (77)

5 (12)

15

Ph-CO(CH2)2

O-CH3

(R)-15b

64 (40)

95 (80)

5 (12)

  1. Unless otherwise stated, all reactions were performed at 30 °C in 1.7 mL PBS buffer (100 mM, pH 7.4) and 0.3 mL ethyl acetate by using 0.1 g SporeE228S-GDH. The substrate concentration was 200 mM
  2. aAbsolute configuration. It was determined by comparing the retention time with that of standard samples
  3. bThe values in parentheses denote the enantioselective synthesis results of 60 mM substrate to the corresponding chiral products with free enzyme in 2.0 mL PBS buffer (100 mM, pH 7.4) at 30 °C