Biotransformation of Nitriles by Marine Fungi 28.3 Results and Discussion 703
Part E | 28.3
Table 28.6 Biotransformation of phenylacetonitrile 1 and 2-cyanopyridine 14 by marine fungus A. sydowii CBMAI 934
a
CN
OH
OH
O
A. sydowii
CBMAI 934
32 °C, 124 rpm
1
1 4
+
+
1a
14a
CN
N
N
O
NH 2
Time (h)
c (%) 1
c(%) 14
c (%) 1a
c (%) 14a
24
100
–
–
–
96 b
–
100
100
100
192
-
19
53
28
a (Sect. 28.2).
b The nitrile 14 was added (Sect. 28.2).
c D concentration of unreacted nitriles 1 and 14 determined by GC-FID analysis.
c D conversion determined by GC-FID analysis.
0
1
2
3
4
5
6
7
8
9
1 0
1 1
1 2
1 4
13
Time
Inten.
Time 8.507 Inten.
38 692
Time Inten.
Time 15.889 Inten.
12 782
–15 000
Time 11.612 Inten.
15 min
µV (×100 000)
µV (×10 000)
Chromatogram
2
1.5
1
0.5
0
5
2.5
0
µV (×10 000)
10
7.5
5
2.5
0
µV (×10 000)
5
2.5
0
µV (×10 000)
a)
b)
c)
d)
e)
2
1
0
CN
CN
CN
CN
N
CN
N
CN
N
OH
OH
O
OH
OH
O
OH
OH
O
N
O
NH 2
N
O
NH 2
N
O
NH 2
Fig. 28.41a–e GC-FID Chromatograms. (a) Standard of benzonitrile 6, 2-cyanopyridine 14 and phenylacetonitrile 1.
(b) Standard of 2-hydroxyphenylacetic acid 1a. (c) Standard of 2-pyridinecarboxamide 14a. (d) Biotransformation
of benzonitrile 6 (20:0 L, 0:19 mmol) and 2-cyanopyridine 14 (20:0 L, 0:21 mmol) by A. sydowii CDMAI 934 in
48 h. (e) Biotransformation of benzonitrile 6 (20:0 L, 0:19 mmol) and 2-cyanopyridine 14 (20:0 L, 0:21 mmol) by A.
sydowii CBMAI 934 in 96 h. Conditions of GC-FID analysis: T i D 100
ı C (2 min), T f D 160
ı C (2 min), r D 5
ı C=min,
t c D 16 min