Skip to main content
. 2008 Aug 7;7:25. doi: 10.1186/1475-2859-7-25

Table 4.

Examples for one step enzymatic reactions employing the designer yeast made by Stewart and coworkers [88,167-170], namely Saccharomyces cerevisiae overexpressing the Acinetobacter sp. NCIB 9871 cyclohexanone monooxygenase. The data is chronologically ordered.

Entry Substrate Product Substrate/Product Code Performance: yield (ee) Ref.
1 Inline graphic Inline graphic a: R = Me a: 83% (≥ 98%) [167,168]
b: R = Et b: 74% (≥ 98%)
c: R = Pri c: 60% (≥ 98%)
d: R = Pr d: 63% (92%)
e: R = allyl e: 62% (95%)

1 2

2 Inline graphic Inline graphic a: R = Me a: 50% (49%) ---I [168,169]
b: R = Et b: 79% (95%) 69% (≥ 98%)
c: R = Pri c: 41% (≥ 98%) 46% (96%)
d: R = Pr d: 54% (97%) 66% (92%)
e: R = allyl e: 59% (≥ 98%) 58% (≥ 98%)
f. R = n-butyl f: 59% (≥ 98%) 64% (98%)

1 2 3

3 Inline graphic Inline graphic a: R = Me a: 71% (≥ 98%) 60 % (≥ 98 %) ---I [168]
b: R = Et b: 18% (70%) 20% (70%) ---I
c: R = Pri c: N.R.II ---I N.R.II
d: R = Pr d: 11% (≥ 98%) ---I 8% (83%)
e: R = allyl e: 15% (97%) ---I 9.3% (≥ 98%)
f. R = n-butyl f: 37% (56%) ---I 11% (84%)

1 2

4 Inline graphic Inline graphic a: R = n-Bu a: 18% (≥ 98%) 32% (≥ 98%) [170]
b: R = n-Hex b: 32% (≥ 98%) 42% (≥ 98%)
c: R = n-Oct c: 25% (≥ 98%) 14% (≥ 98%)
d: R = n- d: 39% (≥ 98%) 37% (≥ 98%)
C11H23

1III 2III 3III

5 Inline graphic Inline graphic a: R = n-Pr a: 27% (13%) -IV (33%) -IV (60%) [170]
b: R = n-Hex overall yield: 44%; ratio 2 : 3 = 83 : 17

b: 54% (29%) (60%) -IV
overall yield: 20%; ratio 2 : 3 = > 99 : < 1

6 Inline graphic Inline graphic a: R = Ph a: 95% (> 99%) [88]
b: R = But b: 47% (99%)
c: R = Bun c: 53% (74%)

7 Inline graphic Inline graphic a: R1 = H
R2 = H
1a: 18% (90%) (2a: 19% yield) [88]
b: R1 = H
R2 = Ph
1b: 30% (30%) (no sulfone 2b detected)

8 Inline graphic Inline graphic a: R1 = H
R2 = H
1a: 20% (75%) [2a: 45% yield] [88]
b: R1 = H
R2 = CH3
1b: 16% (20%) [2b: 15% yield 76% ee]
c: R1 = H
R2 = Ph
1c: 74% (20%) [no sulfone 2c detected]

9 Inline graphic Inline graphic R1 = CH3 1: 84% (48%) [88]
R2 = CH3 2: 10%

IThis isomer was not detected in the product mixture [168];

IIno oxidation detectable [168];

IIIdue to the low enantioselectivities of the reactions, no absolute configuration was assigned [170];

IVvalue not given [170].