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Table 2 Enantioselective synthesis of (R)-PE by SporeE228S-GDH in organic solvents

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

Solvent

Log P

Yield (%)a

ee (%)

Reduction durations

Productivity (mM h−1 g−1)

PBS

 

93 (95)

> 99 (> 99)

4.5 h

429.9 (439.1)

Ethyl acetate

0.68

88 (43)

> 99 (70)

4.5 h (10 h)

406.8 (89.4)

Ethyl acetate (6)b

0.68

72

> 99

27 h

554.7

DMSO

− 1.3

81 (46)

> 99 (85)

4 h (10 h)

421.2 (95.7)

DMSO (3)

− 1.3

70

> 99

12 h

121.3

2-Propanol

0.33

85

98

5 h

353.6

2-Propanol (5)

0.33

70

95

25 h

291.2

Tert-butanol

0.6

72 (41)

96 (82)

5 h (12 h)

299.5 (71.1)

Methylbenzene

2.5

70

98

5 h

291.2

Cyclohexane

3.2

51 (39)

98 (92)

5 h (12 h)

212.2 (67.6)

Nonane

2.9

72

96

5 h

299.5

Hexane

3.5

80

98

4.5 h

369.8

Hexane (3)

3.5

70

93

13.5 h

107.9

Ethyl isovalerate

2.3

68

96

4.5 h

314.3

Urea

− 2.1

82

97

4.5 h

379.0

Urea (4)

− 2.1

70

93

18 h

80.9

  1. Unless otherwise stated, all reactions were performed at 30 °C in 100 mM PBS buffer solution (pH 7.4) by using 0.1 g SporeE228S-GDH. The reaction solution (2 mL) consists of 1.7 mL 100 mM PBS buffer (pH 7.4) and 0.3 mL solvents. AP concentration was 25 g/L (≈ 208 mM)
  2. a(R)-PE synthesis results with free enzymes in 200 mL PBS buffer (100 mM, pH 7.4) are given in parentheses. AP concentration was 8 g/L (≈ 67 mM)
  3. bThe values in parentheses in this column denote the recycled times for enantioselective synthesis