Part E | 28.3
700 Part E Marine Microbiology and Biotechnology
0
1
2
3
4
5
6
7
8
9
1 0
1 1
1 2
1 4
13
Time
Inten.
Time 13.583 Inten. 474 118
Time 14.391 Inten.
48 382
Time 0.455 Inten.
14 688
Time
Inten.
16
15
min
µV (×10 000)
µV (×1 000 000)
Chromatogram
10
7.5
5
2.5
0
1.5
1
0.5
0
µV (×10 000)
5
2.5
0
µV (×10 000)
2
1
0
µV (×1000)
a)
b)
c)
d)
e)
10
5
0
CN
Cl
CN
OH
OH
O
OH
OH
O
Cl
OH
O
Cl
OH
O
Fig. 28.38a–e GC-FID Chromatograms. (a) Standard of 4-chlorophenylacetonitrile 3. (b) Standard of phenylacetonitrile 1. (c) Standard of 2-hydroxyphenylacetic acid 1a. (d) Biotransformation of 4-chlorophenylacetonitrile 3 (60:0 L,
0:47 mmol) by A. sydowii CBMAI 934 in 24 h. (e) 4-Chlorophenylacetic acid 3a purified by flash chromatography.
Conditions of GC-FID analysis: T i D 100
ı C (1 min), T f D 210
ı C (5 min), r D 10
ı C=min, t c D 17 min
Table 28.5 Biotransformation of phenylacetonitrile 1, benzonitrile 6, and 2-cyanopyridine 14 by marine fungus A.
sydowii CBMAI 934
CN
CN
OH
OH
O
A. sydowii
CBMAI 934
32 °C, 124 rpm
1
6
14
+
+
+
1a
14a
CN
N
N
O
NH 2
Time (h)
c (%) 1
c (%) 14
c (%) 6
c (%) 1a
c (%) 14a
24
100
–
–
–
–
96 b
–
100
100
100
–
120
–
65
22
9
4
192
–
61
–
7
32
a (Sect 28.2).
b The nitriles 6 and 14 were added (Sect. 28.2).
c D concentration of unreacted nitriles 1, 6 and 14 determined by GC-FID analysis.
c D conversion determined by GC-FID analysis.