SUPPORTING INFORMATION
Solid-phase Synthesis of the
Aged-Nonapeptide-Nerve-Agent Adduct of Butyrylcholinesterase as
Reference Materials for Analytical Verification
Andreas Bielmann
†,‡, Christophe Curty
†, Christian G. Bochet
‡†
Spiez Laboratory, Austrasse, CH-3700 Spiez, Switzerland
‡
Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg,
Switzerland
[email protected]
Table of Contents
1H NMR,
13C NMR and IR spectra of 6
S2
1H NMR,
13C NMR,
31P NMR and IR spectra of 9
S5
1H NMR,
13C NMR,
31P NMR and IR spectra of 3
S9
1H NMR,
13C NMR,
31P NMR and IR spectra of 11
S13
1H NMR,
13C NMR,
31P NMR and IR spectra of 12
S17
1H NMR,
13C NMR,
31P NMR and IR spectra of 13
S21
1H NMR,
13C NMR,
31P NMR and IR spectra of 4
S25
1H NMR,
13C NMR and IR spectra of 1
S29
1H NMR and
31P NMR spectra and the chromatogram of 2 (route A)
S32
1
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
0.88 1.26 2.18 3.90 3.92 3.99 3.99 4.01 4.02 4.18 4.19 4.21 4.38 4.40 4.42 4.44 4.47 4.48 4.49 5.20 5.78 5.80 7.24 7.29 7.31 7.33 7.37 7.38 7.57 7.59 7.74 7.760.16
0.24
1.01
1.84
1.20
2.96
1.94
0.88
8.62
2.10
2.00
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
ppm
-0.00 14.12 22.65 31.58 42.02 47.00 47.10 53.70 56.15 62.85 63.27 65.14 67.21 67.36 67.53 67.95 76.71 77.03 77.23 77.34 119.68 119.98 120.00 125.08 126.12 127.07 127.09 127.73 128.17 128.31 128.45 128.54 128.65 128.74 128.94 134.78 135.08 141.27 141.32 143.64 143.80 156.25 169.25 170.379.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
1.39 1.44 2.98 3.09 4.20 4.21 4.30 4.32 4.32 4.34 4.36 4.38 4.39 4.41 4.41 4.42 4.44 4.44 4.63 5.29 5.99 7.25 7.28 7.30 7.31 7.32 7.36 7.38 7.58 7.60 7.73 7.752.97
5.01
0.86
1.88
0.84
9.12
2.00
1.90
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
-0.00 10.44 11.90 39.71 42.01 43.34 47.01 53.46 54.47 54.54 55.09 64.73 64.79 65.23 65.58 67.39 67.71 76.72 77.03 77.24 77.35 77.73 119.73 119.95 124.33 124.79 125.17 125.20 125.67 126.10 126.77 127.09 127.39 127.71 128.02 128.16 128.33 128.41 128.51 128.60 128.91 129.07 135.02 135.30 139.72 140.92 141.23 143.71 143.80 155.53 155.99 168.78 169.11160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
34.43
35.21
13.49
11
10
9
8
7
6
5
4
3
2
1
ppm
-0.15 -0.00 0.07 0.15 1.19 1.21 1.22 1.25 1.27 1.28 1.33 1.40 1.43 1.46 1.50 1.51 1.53 1.59 1.66 1.67 1.69 1.72 2.27 2.87 2.94 3.36 3.43 3.47 3.64 3.66 3.69 3.71 3.76 3.88 3.91 3.93 3.95 3.97 3.99 4.04 4.14 4.15 4.17 4.22 4.32 4.33 4.37 4.43 4.53 4.58 4.61 4.70 5.20 6.20 6.67 6.82 6.84 6.98 6.99 7.14 7.16 7.17 7.19 7.23 7.24 7.25 7.26 7.30 7.32 7.33 7.35 7.38 7.45 7.50 7.52 7.53 7.55 7.57 7.69 7.71 7.74 7.75 7.77 8.01 8.07 9.99 10.34 10.713.78
1.11
0.20
0.37
5.79
0.03
0.66
0.17
0.04
4.60
2.07
2.00
0.35
2.12
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
ppm
-0.00 10.34 11.78 46.99 50.77 54.57 65.54 67.47 76.70 77.02 77.22 77.33 119.98 124.74 125.15 127.10 127.75 141.25 143.61 143.75 156.22 172.56160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
32.57
34.17
12.71
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5 ppm
1.45 1.49 4.70 4.94 4.96 4.97 4.99 5.03 5.05 5.06 5.08 7.34 7.36 7.36 7.373.00
0.87
3.95
12.05
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
10.97 12.40 65.23 67.07 67.13 76.72 77.04 77.36 126.95 127.53 127.90 128.41 128.51 128.60 129.70 129.75 136.29 136.35 141.11160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
23.18 23.40 31.740.35
0.32
99.33
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
1.49 1.54 2.09 4.70 5.03 5.05 7.32 7.33 7.33 7.34 7.34 7.35 7.35 7.36 7.37 7.393.00
1.69
0.86
1.89
1.66
1.22
7.29
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
11.15 12.61 20.81 65.35 66.49 66.55 127.01 127.67 127.81 128.38 128.58 136.11 136.18 140.78 176.57160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
31.97
34.65
