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131 Appendix Figure I a. Phylogenetic tree of bacterial isolates 132 Appendix Percent Identity
1
1
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
99.8
99.6
94.0
99.8
99.7
99.8
99.8
93.9
98.9
94.1
99.8
93.6
78.1
99.3
99.2
82.0
94.5
94.8
78.8
78.5
78.8
93.0
92.3
92.2
78.0
84.9
76.6
1
B. cereus AB215098
98.9
93.5
98.6
98.6
98.6
98.6
92.8
96.6
93.0
99.5
93.6
77.9
99.3
99.2
81.5
94.0
94.3
78.8
78.5
78.8
93.0
92.3
92.2
77.2
84.9
76.7
2
B. cereus AF227848
94.1
99.7
99.6
99.7
99.7
94.0
97.6
94.1
99.7
93.6
78.7
99.3
99.2
81.7
94.0
94.3
78.9
78.6
78.8
92.7
92.0
91.8
77.9
85.0
76.7
3
AJ310098.seq
94.2
94.1
94.2
94.2
99.5
93.2
99.7
94.2
99.0
78.1
94.6
94.3
81.1
98.8
99.2
78.3
78.3
78.6
92.3
91.7
91.5
78.0
83.0
75.9
4
B. sonorensis AJ586363
99.9 100.0 100.0 94.1
96.8
94.2 100.0 93.8
78.1
99.3
99.2
81.7
94.0
94.3
78.8
78.5
78.8
93.0
92.3
92.2
78.4
84.9
76.7
5
B. cereus AY224379
94.1
96.8
94.2
93.7
78.0
99.3
99.2
81.7
94.0
94.3
78.7
78.4
78.7
92.9
92.3
92.1
78.3
84.8
76.7
6
B. cereus AY224383
100.0 94.1
96.8
94.2 100.0 93.8
78.1
99.3
99.2
81.7
94.0
94.3
78.8
78.5
78.8
93.0
92.3
92.2
78.4
84.9
76.7
7
B. cereus AY224385
94.1
96.8
94.2 100.0 93.8
78.1
99.3
99.2
81.7
94.0
94.3
78.8
78.5
78.8
93.0
92.3
92.2
78.4
84.9
76.7
8
AY224388.seq
91.9
99.8
94.0
99.3
77.9
94.5
94.2
81.0
98.7
99.1
78.3
78.3
78.6
92.3
91.8
91.6
78.2
83.0
75.6
9
B. licheniformis AY728013
92.3
98.2
94.3
81.0
99.4
99.3
81.2
93.7
94.0
81.8
81.8
83.2
93.0
93.1
92.4
80.3
86.5
79.4
10
B. Cereus DQ884352.seq
94.1
99.4
78.2
94.6
94.3
81.1
98.8
99.2
78.3
78.3
78.6
92.5
91.8
91.6
78.2
83.0
75.9
11
Bacillus sp.EF471917.seq
93.8
78.2
99.3
99.2
81.7
94.0
94.3
78.8
78.5
78.8
93.0
92.3
92.2
78.3
84.9
76.7
12
B. Cereus EU373359.seq
78.2
94.6
94.2
82.4
99.3
99.7
79.0
78.9
78.7
91.9
91.6
91.3
78.2
82.9
75.8
13
B. licheniformis EU373408.
82.1
82.0
98.4
81.1
81.3
98.6
99.9
96.8
77.4
77.3
76.7
94.1
75.9
84.8
14
Staph. haemolyticus EU652064
99.4
81.8
94.0
94.2
82.0
82.0
83.4
93.1
93.2
92.6
82.1
86.8
79.7
15
Fazal-1KWS4.seq
81.7
94.1
94.4
81.9
81.9
83.3
92.9
93.0
80.7
80.8
99.7
99.0
81.4
99.3
81.4
97.1
82.7
81.1
92.8
80.7
92.7
92.4
80.2
82.0
94.6
86.6
78.6
79.6
85.7
16
17
Fazal-2KWS2.seq
Fazal-3 10_1.seq
92.1
81.4
85.0
79.6
18
Fazal-4 DW3.seq
81.7
81.7
82.8
93.1
93.0
92.4
81.4
85.3
79.9
19
Fazal-5 10.seq
98.7
97.2
78.0
78.0
77.2
94.3
76.2
84.6
20
PSU26261.seq
96.9
77.5
77.4
76.8
94.3
75.9
84.8
21
P. stutzeri U26262
77.3
77.8
76.9
95.9
75.6
83.9
22
P. putida D37923.seq
97.8
97.8
76.8
82.4
76.3
23
Staph. aureus D83358
97.6
76.8
83.5
76.3
24
Staph. haemolyticus D83367
76.3
83.1
75.7
25
Staph. hyicus D83368
75.4
84.0
26
P. fluorescens Z76662
74.8
27
Strep. mutans X58303
28
E. coli X80725
2
0.2
3
0.3
1.0
4
6.2
6.7
6.0
5
0.2
1.4
0.3
6.0
6
0.3
1.4
0.3
6.1
0.1
7
0.2
1.4
0.3
6.0
0.0
0.1
8
0.2
1.4
0.3
6.0
0.0
0.1
0.0
9
6.4
7.6
6.2
0.5
6.1
6.2
6.1
6.1
1.1
3.4
2.4
7.2
3.3
3.3
3.3
3.3
8.6
6.2
7.4
6.1
0.3
6.0
6.1
6.0
6.0
0.2
8.2
0.2
0.5
0.3
6.0
0.0
0.1
0.0
0.0
6.2
1.8
6.2
6.7
6.7
6.7
0.9
6.6
6.6
6.6
6.6
0.7
6.0
0.6
6.6
26.0
26.3
25.2
26.0
26.1
26.2
26.1
26.1
26.3
22.0
25.8
26.0
26.0
0.7
0.7
0.7
5.6
0.7
0.7
0.7
0.7
5.7
0.6
5.6
0.7
5.6
20.5
11 12 13 14 15 16 17 10
2
99.9
99.9
99.9
0.8
0.8
0.8
6.0
0.8
0.8
0.8
0.8
6.1
0.7
6.0
0.8
6.1
20.6
0.6
18
20.3
5.7
20.7
6.3
20.5
6.3
21.2
1.2
20.5
6.3
20.5
6.3
20.5
6.3
20.5
6.3
21.4
1.3
21.1
6.6
21.2
1.2
20.5
6.3
20.1
0.7
0.9
22.0
20.3
6.3
20.5
6.2
21.9
19
5.4
5.8
5.8
0.7
5.8
5.8
5.8
5.8
0.8
6.2
0.7
5.8
0.3
21.5
6.0
5.8
21.7
0.2
20
25.0
25.0
24.8
25.7
25.0
25.1
25.0
25.0
25.8
21.0
25.8
25.0
24.8
1.4
20.7
20.8
0.7
21.5
21.2
21
25.5
25.5
25.3
25.7
25.5
25.6
25.5
25.5
25.8
21.0
25.8
25.5
24.9
0.1
20.7
20.8
0.5
21.5
21.2
1.3
22
25.1
25.1
25.0
25.3
25.1
25.2
25.1
25.1
25.4
19.2
25.4
25.1
25.2
3.2
18.9
19.0
2.9
19.8
19.7
2.8
3.2
23
7.4
7.4
7.7
8.1
7.4
7.5
7.4
7.4
8.2
7.5
8.0
7.4
8.6
27.0
7.3
7.6
21.6
7.7
7.3
26.1
26.9
27.2
24
8.2
8.2
8.5
8.8
8.2
8.3
8.2
8.2
8.7
7.3
8.7
8.2
9.0
27.3
7.2
7.4
22.2
7.8
7.5
26.2
27.1
26.6
2.2
8.3
8.3
8.7
9.1
8.3
8.4
8.3
8.3
9.0
8.1
9.0
8.3
9.4
28.2
7.9
8.2
23.0
8.4
8.1
27.5
28.0
27.8
2.3
2.5
25.6
26.7
25.6
25.5
25.0
25.1
25.0
25.0
25.3
22.7
25.4
25.2
25.2
5.6
20.3
20.4
4.7
21.3
21.1
5.4
5.4
3.6
27.4
27.4
28.1
14.7
14.7
14.6
17.1
14.7
14.8
14.7
14.7
17.2
13.2
17.2
14.7
17.3
26.9
12.7
13.0
23.2
15.0
14.6
26.5
26.9
27.4
17.9
16.5
17.0
27.0
27.9
27.8
27.8
29.0
27.8
27.8
27.8
27.8
29.5
24.0
29.0
27.8
29.2
16.8
23.5
23.6
15.5
23.6
23.3
17.1
16.9
17.9
28.4
28.4
29.4
17.2
28.3
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
26 27 28 25
28
Figure I b. Percent identity of bacterial isolates with other known identified bacterial strains
133 Appendix (Continued on next page) 134 Appendix Figure I c. nidAB gene sequence cloned from Mycobacterium PY146 and containing
the EcoRI and HindIII restriction enzyme adaptor sequences
135 Appendix Ab und ance
A
Scan 2744 (18.758 min): 0201002.D\ d ata .ms (-2724) (-)
115.0
7000000
6500000
144.0
6000000
5500000
5000000
4500000
4000000
3500000
3000000
2500000
2000000
1500000
1000000
89.0
63.0
500000
39.0
72.0
50.0
98.0
0
30
40
50
60
70
80
90
100
126.0135.0
110
120
130
140
m/ z-->
B
100
144
115
50
HO
89
63
39
50
72
98
0
30 40 50 60
(replib) 2-Naphthalenol
70
80
126
90 100 110 120 130 140
Figure II a. Mass spectra obtained by GC/MS of 2-Naphthalenol produced by Bacillus
cereus KWS2 grown with naphthalene (A) and from NIST mass spectral library (B).
136 Appendix Ab und a nce
A
Sca n 2046 (15.025 min): 0201002.D\ d a ta .ms (-2025) (-)
91.0
200000
180000
160000
140000
120000
100000
80000
135.9
60000
40000
65.0
20000
39.0
51.0
77.0
107.1 117.9126.0
0
30
40
50
60
70
80
90
100
110
120
130
140
m/ z-->
B
91
100
O
OH
50
136
0
39 45 51
65
77
30 40 50 60 70
(replib)
Benzeneacetic acid
80
90 100 110 120 130 140
Figure II b. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Bacillus cereus KWS2 grown with naphthalene (A) and from NIST mass spectral
library (B).
137 Appendix A
Ab und a nc e
Sc a n 1797 (13.693 min): 0201002.D \ d a ta .ms
105.0
8000
121.9
7500
7000
76.9
6500
6000
5500
5000
4500
4000
3500
3000
2500
43.0
51.0
2000
1500
59.9
1000
69.1
500
91.0
84.1
0
30
35
40
45
50
55
60
65
70
75
80
85
90
95 100105110115120125
m/ z-->
B
105
100
122
77
HO
O
51
50
39
45
94
65
0
30
40
50
60
70
(mainlib) Benzenecarboxylic acid
80
90
100
110
120
Figure II c. Mass spectra obtained by GC/MS of Benzenecarboxylic acid produced by
Bacillus cereus KWS2 grown with naphthalene (A) and from NIST mass spectral
library (B).
138 Appendix Ab und ance
A
Sca n 1153 (10.249 min): 0201002.D\ d ata .ms (-1141) (-)
130000
106.0
120000
110000
77.0
100000
90000
80000
70000
60000
51.0
50000
40000
30000
20000
39.0
10000
63.1
45.2
0
30
35
40
45
50
55
60
65
82.7 88.9
70
75
80
85
90
95.8
95 100 105
m/ z-->
B
106
77
100
O
51
50
0
30
39
74
43
30
40
50
(replib) Benzaldehyde
63
60
84 89
70
80
90
100
Figure II d. Mass spectra obtained by GC/MS of Bezaldehyde produced by Bacillus
cereus KWS2 grown with naphthalene (A) and from NIST mass spectral library (B).
139 Appendix A
A b und a nc e
S c a n 4002 (25.487 m in): 0201002.D \ d a ta .m s (-4009) (-)
194.0
165.0
700000
650000
600000
550000
500000
450000
400000
350000
300000
250000
200000
150000
100000
82.1
139.0
50000
69.4
39.0
97.0
115.0
51.0
127.0
0
30
40
50
60
70
80
90
151.0
181.8
100 110 120 130 140 150 160 170 180 190
m/ z-->
B
194
100
165
50
0
37 49
69
82
OH
97
30
50
70
90
(mainlib)
9-Phenanthrenol
115 126 139 150
110
130
150
174
170
190
Figure II e. Mass spectra obtained by GC/MS of 9-phenanthrenol produced by
Bacillus cereus KWS2 grown in phenanthrene (A) and from NIST mass spectral
library (B).
140 Appendix A
A b und a nc e
S c a n 3946 (25.187 m in): 0201002.D \ d a ta .ms (-3932) (-)
165.0
170000
160000
150000
140000
130000
120000
181.0
110000
212.0
100000
90000
80000
70000
60000
193.9
50000
152.0
40000
30000
20000
76.9
10000
115.0
63.0
49.9
138.9
101.9
0
30
40
50
60
70
80
90
100 110 120 130 140 150 160 170 180 190 200 210
m/ z-->
B
165
100
212
181
50
82
51 63
69
0
41
194
HO
OH
115
89
151
139
30
50
70
90 110 130 150 170
(mainlib)
9,10-Dihydro-9,10-dihydroxyphenanthrene
190
210
Figure II f. Mass spectra obtained by GC/MS of 9, 10-dihydro-9, 10dihydroxyphenanthrene produced by Bacillus cereus KWS2 grown in phenanthrene
(A) and from NIST mass spectral library (B).
141 Appendix A
A b und a nc e
S c a n 2058 (15.089 min): 0201002.D \ d a ta .ms (-2025) (-)
91.0
400000
380000
360000
340000
320000
300000
280000
260000
240000
220000
200000
180000
160000
140000
135.9
120000
100000
80000
65.0
60000
40000
39.0
51.0
20000
77.0
98.8 106.9
0
30
40
50
60
70
80
90
100
110
118.0
120
128.2
130
m / z-->
B
91
100
O
OH
50
136
0
39 45 51
65
77
30 40 50 60 70
(replib)
Benzeneacetic acid
80
90 100 110 120 130 140
Figure II g. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Bacillus cereus KWS2 grown in phenanthrene (A) and from NIST mass spectral
library (B).
142 Appendix A
Ab und a nce
Sca n 2856 (19.357 min): 0301003.D \ d a ta .ms (-2816) (-)
107.0
1100000
1000000
900000
800000
700000
600000
500000
400000
151.9
300000
77.0
200000
100000
51.0
39.0
63.0
89.0 98.0
0
30
40
50
60
70
80
90
129.0
116.9
100
110
120
141.2
130
140
150
m/ z-->
B
107
100
O
OH
50
152
77
0
31 39
51
OH
63
86 95
121
134
30 40 50 60 70 80 90 100 110 120 130 140 150
(mainlib)
Benzeneacetic acid, 4-hydroxy Figure II h. Mass spectra obtained by GC/MS of 4-hydroxy benzeneacetic acid
produced by Bacillus cereus KWS2 grown in phenanthrene (A) and from NIST mass
spectral library (B).
143 Appendix A
A b und a nc e
S c a n 1862 (14.041 min): 2301024.D \ d a ta .ms (-1871) (-)
105.0
95000
90000
85000
122.0
80000
75000
70000
65000
60000
77.0
55000
50000
45000
40000
35000
30000
51.0
25000
20000
15000
10000
39.0
5000
60.0
94.1
85.0
69.0
115.0
0
25
30
35
40
45
50
55
60
65
70
75
80
85
90
95 100105110115120
m/ z-->
B
105
100
HO
122
O
77
50
51
39 45
74
65
94
0
30
40
50
60
70
(replib) Benzenecarboxylic acid
80
90
100
110
120
Figure II i. Mass spectra obtained by GC/MS of benzenecarboxylic acid produced by
Bacillus cereus KWS2 grown in anthracene (A) and from NIST mass spectral library
(B).
144 Appendix Ab und a nce
A
Sca n 2088 (15.250 min): 2301024.D\ d a ta .ms (-2075) (-)
91.0
220000
200000
180000
160000
140000
120000
100000
136.0
80000
60000
101.0
40000
65.0
39.0
20000
116.0
75.0
51.0
128.1
0
30
40
50
60
70
80
90
100
110
120
130
m/ z-->
B
91
100
O
OH
50
136
65
0
39 46 51
56
72 77
30 40 50 60 70
(replib)
Benzeneacetic acid
80
101
90
117
100 110 120 130 140
Figure II j. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Bacillus cereus KWS2 grown in anthracene (A) and from NIST mass spectral library
(B). 145 Appendix A
A b und a nc e
S c a n 2856 (19.357 min): 2301024.D \ d a ta .ms (-2826) (-)
107.0
800000
750000
700000
650000
600000
550000
500000
450000
400000
350000
300000
152.0
250000
200000
77.0
150000
100000
51.1
50000
39.1
63.0
89.0
0
30
40
50
60
70
80
90
123.1
100
110
120
141.9
130
140
150
m/ z-->
B
107
100
O
OH
50
152
77
0
31 39
51
63
OH
86 95
121
134
30 40 50 60 70 80 90 100 110 120 130 140 150
(mainlib)
Benzeneacetic acid, 4-hydroxy Figure II k. Mass spectra obtained by GC/MS of 4-hydroxy benzeneacetic acid
produced by Bacillus cereus KWS2 grown in anthracene (A) and from NIST mass
spectral library (B).
146 Appendix A
A b und a nc e
S c a n 2740 (18.737 m in): 0601006.D \ d a ta .ms (-2721) (-)
115.0
3200000
144.0
3000000
2800000
2600000
2400000
2200000
2000000
1800000
1600000
1400000
1200000
1000000
800000
600000
89.0
400000
63.0
200000
39.0
74.0
50.0
98.0
126.0134.8
0
30
40
50
60
70
80
90
100
110
120
130
140
m / z-->
B
100
144
115
50
HO
89
63
39
50
72
98
0
30 40 50 60
(replib) 2-Naphthalenol
70
80
126
90 100 110 120 130 140 150
Figure III a. Mass spectra obtained by GC/MS of 2-naphthalenol produced by
Bacillus cereus KWS4 grown with naphthalene (A) and from NIST mass spectral
library (B).
147 Appendix A b und a nc e
S c a n 2045 (15.020 min): 0601006.D \ d a ta .ms (-2021) (-)
91.0
180000
A
170000
160000
150000
140000
130000
120000
110000
100000
90000
80000
70000
135.9
60000
50000
40000
65.0
30000
20000
39.0
51.0
10000
76.9
99.8 108.0 118.0 127.9
0
30
40
50
60
70
80
90
100
110
120
130
140
m/ z-->
B
91
100
O
OH
136
50
65
39
44
51
77
105
0
30 40 50 60 70
(mainlib) Benzeneacetic acid
80
90
118
100 110 120 130 140
Figure III b. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Bacillus cereus KWS4 grown with naphthalene (A) and from NIST mass spectral
library (B).
148 Appendix Ab und a nce
A
Sca n 1151 (10.238 min): 0601006.D \ d a ta .ms (-1140) (-)
106.0
77.0
20000
18000
16000
14000
12000
10000
51.0
8000
6000
4000
2000
39.0
62.9
45.0
0
30
35
40
45
50
55
60
88.0
70.9
65
70
75
80
85
90
95
100 105
m/ z-->
B
106
77
100
O
51
50
0
30
39
74
43
30
40
50
(replib) Benzaldehyde
63
60
84 89
70
80
90
100
Figure III c. Mass spectra obtained by GC/MS of Bezaldehyde produced by Bacillus
cereus KWS4 grown with naphthalene (A) and from NIST mass spectral library (B).
149 Appendix A
Ab und a nc e
S c a n 4002 (25.487 min): 0401004.D \ d a ta .ms (-4012) (-)
165.0
194.0
1050000
1000000
950000
900000
850000
800000
750000
700000
650000
600000
550000
500000
450000
400000
350000
300000
250000
200000
150000
82.2
139.0
100000
69.4
50000
97.0
39.0 51.0
0
30
40
50
60
70
80
90
115.0
127.0
150.9
179.9
100 110 120 130 140 150 160 170 180 190
m/ z-->
B
165
100
194
50
82
39 50
69
OH
87 97
0
30
50
70
(replib) 9-Phenanthrenol
90
115 126
110
139
130
150
150
174
170
190
Figure III d. Mass spectra obtained by GC/MS of 9-phenanthrenol produced by
Bacillus cereus KWS4 grown in phenanthrene (A) and from NIST mass spectral
library (B). 150 Appendix A
A b und a nc e
S c a n 3947 (25.193 min): 0401004.D \ d a ta .m s (-3931) (-)
165.0
200000
190000
180000
170000
160000
150000
140000
181.0
130000
120000
212.0
110000
100000
90000
80000
70000
60000
151.9
50000
40000
30000
77.0
20000
194.9
115.0
138.9
63.0
10000
50.0
0
101.8
36.9
30
40
50
60
70
80
90
100 110 120 130 140 150 160 170 180 190 200 210
m/ z-->
B
165
100
212
181
50
82
51 63
69
0
41
194
HO
89
OH
115
151
139
30
50
70
90 110 130 150 170
(mainlib) 9,10-Dihydro-9,10-dihydroxyphenanthrene
190
210
Figure III f. Mass spectra obtained by GC/MS of 9,10-dihydro-9,10dihydroxyphenanthrene produced by Bacillus cereus KWS4 grown in phenanthrene
(A) and from NIST mass spectral library (B). 151 Appendix A
Ab und a nc e
Sc a n 2065 (15.127 min): 0401004.D \ d a ta .ms (-2026) (-)
91.0
600000
550000
500000
450000
400000
350000
300000
250000
135.9
200000
150000
65.0
100000
39.0
50000
51.0
77.0
107.0
0
30
40
50
60
70
80
90
100
110
117.8 126.8
120
130
m/ z-->
B
91
100
O
OH
50
136
0
39 45 51
65
77
30 40 50 60 70
(replib) Benzeneacetic acid
80
90
100 110 120 130
Figure III g. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Bacillus cereus KWS4 grown in phenanthrene (A) and from NIST mass spectral
library (B). 152 Appendix A
Ab und a nc e
Sc a n 2841 (19.277 min): 0501005.D \ d a ta .ms (-2810) (-)
107.0
170000
160000
150000
140000
130000
120000
110000
100000
90000
80000
70000
151.9
60000
50000
77.0
40000
30000
63.0
51.0
20000
86.9
125.9
39.0
10000
97.9
0
30
40
50
60
70
80
90
100
134.9
116.0
110
120
130
140
150
m/ z-->
B
107
100
O
OH152
50
77
39
0
30
51
HO
63
90
124 134
30 40 50 60 70 80 90 100 110 120 130 140 150
(replib)
Benzeneacetic acid, 3-hydroxy Figure III h. Mass spectra obtained by GC/MS of 3-hydroxy benzeneacetic acid
produced by Bacillus cereus KWS4 grown in phenanthrene (A) and from NIST mass
spectral library (B). 153 Appendix A
Ab und a nc e
Sca n 2218 (15.945 min): 0501005.D \ d a ta .ms (-2210) (-)
92.0
119.9
60000
55000
50000
45000
40000
137.9
35000
30000
25000
20000
64.0
43.0
15000
10000
53.0
72.0
5000
0
80.8
105.1
35.1
30
40
50
60
70
80
90
100
110
127.9
120
130
140
m/ z-->
B
92
100
120
O
OH
138
50
OH
64
39
45
53
74 81
109
0
30 40 50 60 70 80
(replib) Benzoic acid, 2-hydroxy-
90
100 110 120 130 140
Figure III i. Mass spectra obtained by GC/MS of 2-hydroxy benzoic acid produced by
Bacillus cereus KWS4 grown in phenanthrene (A) and from NIST mass spectral
library (B).
154 Appendix A
Abundance
Scan 1857 (17.014 min): 2001005.D\ data.ms
104.0
600000
550000
500000
450000
76.0
400000
350000
300000
250000
200000
50.0
150000
148.0
100000
50000
38.0
61.0
85.0
0
30
40
50
60
70
80
116.0
94.8
90
100
110
120
128.9 138.0
130
140
m/ z-->
B
104
100
O
76
OH
50
OH
50
O
0
31
38
61
148
85
30 40 50 60 70 80 90 100 110 120 130 140 150
(rep
lib
) 1,2-Benzened icarb oxylic acid
Figure IV a. Mass spectra obtained by GC/MS of 1, 2-benzenecarboxylic acid
produced by resting cells of Mycobacterium PY146 with phenanthrene (A) and from
NIST mass spectral library (B).
155 Appendix Abundance
A
Scan 1865 (17.057 min): 2201007.D\ data.ms (-1849) (-)
104.0
30000
28000
26000
24000
22000
76.0
20000
18000
16000
14000
12000
10000
8000
148.0
50.1
6000
4000
37.2
2000
60.8
30
40
50
60
116.7 126.9
93.0
0
70
80
90
100
110
120
130
140
m/ z-->
B
104
100
O
76
OH
50
OH
50
O
0
31
38
61
148
85
30 40 50 60 70 80 90 100 110 120 130 140 150
(rep lib ) 1,2-Benzened icarb oxylic a cid
Figure IV b. Mass spectra obtained by GC/MS of 1,2-benzenecarboxylic acid
produced by resting cells of Mycobacterium PY146 with anthracene (A) and from
NIST mass spectral library (B).
156 Appendix A
Abundance
Scan 3359 (25.048 m
in): 2101006.D\ data.m
s
208.0
160000
150000
140000
180.0
130000
120000
110000
100000
152.0
90000
80000
70000
60000
50000
40000
76.0
30000
20000
50.0
10000
0
126.0
63.0
90.0
111.0
30
40
50
60
70
80
90
194.0
165.0
139.0
36.8
100 110 120 130 140 150 160 170 180 190 200
m
/ z-->
B
208
100
180
O
152
50
76
O
0
39
50 63
90
99
30
50
70
90
110
(replib)
9,10-Anthracenedione
126
130
163
150
170
190
210
Figure IV c. Mass spectra obtained by GC/MS of 1,2-benzenecarboxylic acid
produced by resting cells of Mycobacterium PY146 with anthracene (A) and from
NIST mass spectral library (B).
157 Appendix A
Abundance
Scan 1861 (17.035 min): 2401009.D\ data.ms (-1849) (-)
104.0
40000
35000
30000
76.0
25000
20000
15000
10000
50.0
148.0
5000
38.1
61.1
87.1
113.0
0
30
40
50
60
70
80
90
100
110
124.9 133.7
120
130
140
m/ z-->
B
104
100
O
76
OH
50
OH
50
O
0
31
38
61
148
85
30 40 50 60 70 80 90 100 110 120 130 140 150
(replib)
1,2-Benzenedicarb oxylic acid
Figure IV d. Mass spectra obtained by GC/MS of 1,2-benzenecarboxylic acid
produced by resting cells of Mycobacterium PY146 with pyrene (A) and from NIST
mass spectral library (B). 158 Appendix A
Abundance
Scan 4817 (32.846 m
in): 2301008.D\ data.m
s
218.0
24000
23000
22000
21000
20000
19000
18000
17000
16000
15000
14000
13000
12000
11000
189.0
10000
9000
8000
7000
6000
5000
4000
3000
43.0
2000
1000
57.1
72.9
94.1
111.0
130.0
147.0
163.1
203.0
0
30
40
50
60
70
80
90
100 110 120 130 140 150 160 170 180 190 200 210 220
m
/ z-->
B
218
100
OH
189
50
94
81
109
163
0
30
50
70
90
(rep
lib
)
1-Hyd
roxypyrene
110
130
150
170
190
210
Figure IV e. Mass spectra obtained by GC/MS of 1-hydroxypyrene produced by
resting cells of Mycobacterium PY146 with pyrene (A) and from NIST mass spectral
library (B). 159 Appendix Ab und a nc e
A
2600000
Sc a n 2241 (16.068 min): 1701018.D \ d a ta .ms (-2216) (-)
104.0
2400000
2200000
76.0
2000000
1800000
1600000
1400000
1200000
1000000
50.1
800000
600000
148.0
400000
38.1
200000
61.0
85.0
0
30
40
50
60
70
80
94.9
90
118.9 129.0 139.0
100
110
120
130
140
m/ z-->
B
104
100
O
76
OH
50
OH
50
O
0
31
38
61
148
85
30 40 50 60 70 80 90 100 110 120 130 140 150
(replib) 1,2-Benzenedicarboxylic acid
Figure V a. Mass spectra obtained by GC/MS of 1,2-benzenedicarboxylic acid
produced by Mycobacterium PY146 grown in phenanthrene (A) and from NIST mass
spectral library (B). 160 Appendix Ab und a nce
A
450000
Sca n 2068 (15.142 min): 1901020.D\ d a ta .ms (-2034) (-)
91.0
400000
350000
300000
250000
200000
136.0
150000
100000
65.0
50000
39.1
51.0
77.0
98.9 107.0
0
30
40
50
60
70
80
90
100
110
117.9
120
130
m/ z-->
B
91
100
O
OH
50
136
0
39 45 51
65
30 40 50 60 70
(replib)
Benzeneacetic acid
77
80
90
100 110 120 130
Figure V b. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Mycobacterium PY146 grown in phenanthrene (A) and from NIST mass spectral
library (B). 161 Appendix A
A b und a nc e
Sc a n 3709 (23.920 min): 3001031.D \ d a ta .ms (-3691) (-)
180.0
90000
208.0
85000
80000
75000
70000
65000
152.0
60000
55000
50000
45000
40000
35000
30000
76.0
25000
20000
15000
50.0
10000
126.0
63.0
5000
0
97.9
111.0
37.0
30
40
50
60
70
80
90
194.9
100 110 120 130 140 150 160 170 180 190 200
m/ z-->
B
152
100
180
208
O
76
50
O
50
63
0
39
126
90 102
30
50
70
90 110
(replib) 9,10-Anthracenedione
130
150
170
190
210
Figure V c. Mass spectra obtained by GC/MS of 9,10-anthracenedione produced by
Mycobacterium PY146 grown in anthracene (A) and from NIST mass spectral library
(B). 162 Appendix Ab und a nce
A
Sca n 1834 (13.891 min): 3101032.D \ d a ta .ms (-1788) (-)
105.0
50000
45000
122.0
40000
77.0
35000
30000
25000
20000
51.0
15000
10000
43.1
87.0
60.0
5000
94.0
70.0
115.1
0
25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100105110115120
m/ z-->
B
105
100
HO
122
O
77
50
51
39 45
65
74
94
0
30
40
50
60
70
(replib)
Benzenecarboxylic
acid
80
90
100
110
120
Figure V d. Mass spectra obtained by GC/MS of benzenecarboxylic acid produced by
Mycobacterium PY146 grown in anthracene (A) and from NIST mass spectral library
(B). 163 Appendix A
Ab und a nc e
Sc a n 2080 (15.207 min): 3101032.D \ d a ta .ms (-2031) (-)
91.0
700000
650000
600000
550000
500000
450000
400000
350000
300000
136.0
250000
200000
150000
65.0
100000
39.1
50000
51.0
77.0
99.0 107.0
0
30
40
50
60
70
80
90
100
110
118.0 127.8
120
130
m/ z-->
B
91
100
O
OH
50
136
0
39 45 51
65
30 40 50 60 70
(replib) Benzeneacetic acid
77
80
90
100 110 120 130
Figure V e. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Mycobacterium PY146 grown in anthracene (A) and from NIST mass spectral library
(B). 164 Appendix A
A b und a nc e
S c a n 2234 (16.030 min): 3101032.D \ d a ta .ms (-2218) (-)
104.0
200000
190000
180000
170000
160000
150000
76.0
140000
130000
120000
110000
100000
90000
80000
70000
50.0
60000
50000
40000
147.9
30000
20000
38.0
10000
61.0
0
20
30
40
50
60
112.9122.1
92.1
70
80
90
100
110
120
136.0
130
140
150
m/ z-->
B
104
100
O
76
OH
50
OH
50
O
0
31
38
61
148
85
30 40 50 60 70 80 90 100 110 120 130 140 150
(replib) 1,2-Benzenedicarboxylic acid
Figure V f. Mass spectra obtained by GC/MS of 1,2-benzenedicarboxylic acid
produced by Mycobacterium PY146 grown in anthracene (A) and from NIST mass
spectral library (B). 165 Appendix A
Ab und a nc e
Sc a n 1614 (12.956 min): 0501005.D \ d a ta .ms (-1598) (-)
105.0
122.0
55000
50000
45000
77.0
40000
35000
30000
25000
20000
51.1
15000
87.0
10000
60.0
5000
94.0
69.0
113.0
0
45
50
55
60
65
70
75
80
85
90
95
100 105 110 115 120
m/ z-->
B
105
100
122
77
HO
O
51
50
65
74
90
0
50
60
70
80
(mainlib) Benzenecarboxylic acid
90
94
100
110
120
Figure V g. Mass spectra obtained by GC/MS of benzenecarboxylic acid produced by
Mycobacterium PY146 grown in pyrene (A) and from NIST mass spectral library (B). 166 Appendix Ab und a nce
A
Sc a n 1887 (14.373 min): 0501005.D \ d a ta .ms
91.1
900000
800000
700000
600000
500000
400000
136.0
300000
200000
65.1
79.1
100000
51.1
58.0
0
98.1
72.1
122.0
107.1 115.0
129.1
40 45 50 55 60 65 70 75 80 85 90 95 100105110115120125130135
m/ z-->
B
91
100
O
OH136
50
65
51
63
89
77
105
0
50
60
70
80
(mainlib)
Benzeneacetic
acid
90
100
110
118
120
130
140
Figure V h. Mass spectra obtained by GC/MS of benzeneacetic acid produced by
Mycobacterium PY146 grown in pyrene (A) and from NIST mass spectral library (B). 167 Appendix A
Ab und a nc e
Sc a n 2014 (15.032 min): 0501005.D \ d a ta .ms (-1993) (-)
104.0
1300000
1200000
1100000
1000000
76.0
900000
800000
700000
600000
500000
50.1
400000
300000
148.0
200000
100000
61.0
85.0
0
40
50
60
70
80
118.9127.1 136.8
93.0
90
100
110
120
130
140
m/ z-->
B
104
100
O
76
OH
50
50
OH
148
O
0
61 66
85
50 60 70 80 90 100 110 120
(replib) 1,2-Benzenedicarboxylic acid
130 140 150
Figure V i. Mass spectra obtained by GC/MS of 1,2-benzenedicarboxylic acid
produced by Mycobacterium PY146 grown in pyrene (A) and from NIST mass
spectral library (B). 168 
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