Y.-F. Chang, D.-F. Tai / Tetrahedron: Asymmetry 12 (2001) 177–179
179
Table 2. Comparison of the enantioselectivity of lipase OF I and lipase OF II on the hydrolysis of 2-chloroethyl
a-arylpropionates at various pH
Entry
Enzyme
Ester
pH
Duration (h)
E.e. (%)
E.e.p (%)
Conversion (%)
Ep10
s
7
8
9
Lipase OF I
Lipase OF I
Lipase OF I
Lipase OF I
Lipase OF I
1
1
2
3
3
3
6
6
6
8
48
104
20
72
72
0
0
0
24
40
19
7
0
104
137
397
7
20.4(R)
46.6(R)
29.3(R)
8.6(R)
97.7(S)
97.2(S)
99.4(S)
73.3(S)
10
1
1
12
13
14
15
16
Lipase OF II
Lipase OF II
Lipase OF II
Lipase OF II
Lipase OF II
1
1
2
3
3
3
6
6
3
8
36
40
20
56
20
30.7(R)
88.6(R)
39.8(R)
19.1(R)
42.7(R)
99.5(S)
45.9(S)
42.2(S)
93.6(S)
71.0(S)
24
40
51
20
45
576
7
4
36
9
Table 3. Enantioselectivity of lipase OF III in the resolution of 2-chloroethyl esters
Entry
Enzyme
Ester
pH
Duration (h)
E.e. (%)
E.e.p (%)
Conversion (%)
Ep10
s
17
18
19
20
21
Lipase OF III
Lipase OF III
Lipase OF III
Lipase OF III
Lipase OF III
1
1
2
3
3
3
7.5
6
2.6
8
48
18
20
72
96
0
0
0
42
33
0
0
1
5
0
23
0.5(S)
23.4(R)
0
10.5(R)
59.5(S)
0
92.3(S)
75.1(R)
58
lectivity compared to the crude enzyme. We have fur-
thermore identified the isozymes at different pH that
control, independently, the enantioselectivity and the
overall catalytic activity of the lipase.
4. (a) Wu, S.-H.; Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc.
1990, 112, 1990–1995; (b) Brahimi-Horn, M. C.;
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This work was financially supported by the National
Science Council of Taiwan (NSC 86-2113-M-259-007).
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