practical synthesis of maleimides and coumarin-linked ... · 1 supporting information practical...
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Supporting Information Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides
Hong Y. Song,a,b Mun H. Ngai,a Zhen Y. Song,c Paul A. MacAry,c Jonathan Hobleyb and Martin J. Lear*a
a Department of Chemistry, and Medicinal Chemistry Program of the Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543. E-mail: chmlmj@nus.edu.sg b Institute of Materials Research and Engineering, 3 Research Link, Singapore 117602 c Immunology Programme, Centre for Life Sciences, National University of Singapore, 28 Medical Drive, Singapore 117456
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
2
2a
2.0
00
0
1.8
31
4
Inte
gra
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6.0
78
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3.6
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2.5
06
02
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2.4
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(ppm)
0.00.40.81.21.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.68.08.48.89.29.6
ju211017.2
N
O
O
COOH
2a
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
3
2a
16
9.5
54
01
67
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(ppm)
102030405060708090100110120130140150160170180190
ju201013.2
N
O
O
COOH
2a
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
4
2b
2.0
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143
2.0
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6.0
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2.5
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2.5
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0.00.40.81.21.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.68.08.48.89.29.6
ju231019.3
N
O
O
2b
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
5
2b
172.4
923
167.8
594
136.5
346
40.8
291
40.5
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40.2
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40.0
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39.7
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39.4
400
39.1
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35.3
598
32.0
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(ppm)
102030405060708090100110120130140150160170180190
ju231019.4
N
O
O
2b
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
6
2c
2.0
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2.1
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2.1
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2.1
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Inte
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6.0
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2.8
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(ppm)
0.00.40.81.21.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.68.08.48.89.29.6
fe10shy1.1 (1091)
N
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2c
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
7
2c
17
4.2
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33
23
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48
(ppm)
102030405060708090100110120130140150160170180190
ju261091.2
N
O
O
2c
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
8
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1.1
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2.2
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fe10shy3.1 (1095)
N
O
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2d
HN
O
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
9
2d
171.3
214
167.8
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166.8
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41.2
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39.1
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(ppm)
102030405060708090100110120130140150160170180190
fe10shy3.2 (1095 13C)
N
O
O
2d
HN
O
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
10
2e
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ja302131.1 (2-131)
N
O
O
2e
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
11
2e
167.8
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136.6
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49.8
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(ppm)
102030405060708090100110120130140150160170180190
ju25yge.5 1025
N
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O
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
12
3a.
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sg1005shy2.5 (1069-2) (b-ala)
3a
N
O
O
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N
O
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
13
3a
17
0.9
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81
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1520253035404550556065707580859095100105110115120125130135140145150155160165170175
sg1005shy2.6 (1069-2)
3a
N
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O
N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
14
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1.7
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1H AMX500 mh0211 sh3b 1
N
O
O
3b
O
O
N
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
15
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(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175
13C AMX500 mh0211 sh3b 2
N
O
O
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N
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
16
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1.8
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(ppm)
0.20.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.8
1H AMX500 mh0210_5135 sh6c 2
1.7
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1.7
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1.7
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1.7
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1.6
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1.3
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1.3
769
1.3
617
(ppm)
1.301.401.501.601.701.80
N
O
O
O
O
N
O
O
3c
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
17
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17
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5101520253035404550556065707580859095100105110115120125130135140145150155160165170175
13C AMX500 mh0210_5135 sh6c 4
N
O
O
O
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N
O
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3c
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
18
3d
2.1
117
2.0
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4.1
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Inte
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8.2
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8.2
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0.00.40.81.21.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.68.08.48.89.29.6
ja29shy.1 2-131
N
O
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3d
O
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
19
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102030405060708090100110120130140150160170180190
ja29shy.2 2-131
N
O
O
3d
O
O N
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
20
1.0
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1.0
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0.9
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3.6
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2.3
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1.2
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0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
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7.4
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7.3
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(ppm)
5.86.06.26.46.66.87.07.27.47.6
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
21
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77.4
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fe171103-5 13C
O ON
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
22
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
23
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
24
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
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39.1
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(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175180185190195
sg06261005.2
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Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
26
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22
(ppm)
1.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.48.6
sg1023shy1.1 (1065 1H)
O ON
NH
ONH
O
2
O
N
O
O
6
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
27
6
17
1.2
23
71
70
.01
40
16
8.4
39
9
16
1.1
96
3
15
5.8
54
6
15
3.2
74
91
51
.83
20
13
5.0
20
0
12
6.4
93
8
10
9.7
69
31
09
.46
32
10
8.6
98
1
97
.94
92
70
.03
85
69
.99
48
69
.48
47
69
.46
28
40
.50
28
40
.26
23
40
.16
76
40
.00
00
39
.83
97
39
.50
45
39
.35
87
39
.21
30
38
.95
79
34
.54
18
34
.42
52
(ppm)
253035404550556065707580859095100105110115120125130135140145150155160165170175
sg1023shy1.2 (13C 1065)
O ON
NH
ONH
O
2
O
N
O
O
6
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
28
6
13
4.9
94
8
12
6.4
68
6
10
9.7
44
11
09
.43
80
97
.92
40
70
.01
33
69
.96
96
69
.45
95
69
.43
76
40
.17
88
39
.33
35
39
.18
77
38
.93
27
34
.51
65
34
.39
27
(ppm)
253035404550556065707580859095100105110115120125130135140145150155160165170175
DEPT135 sg1023shy1.3 (1065)
O ON
NH
ONH
O
2
O
N
O
O
6
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
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