Embed Size (px)
Citation preview
1
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: [email protected] 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
l
6.0
78
0
3.6
70
8
2.5
06
02
.50
00
2.4
94
0
(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
.68
49
13
5.5
09
1
40
.83
64
40
.55
28
40
.27
64
40
.00
00
39
.72
36
39
.44
73
39
.16
36
(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
000
2.1
143
2.0
408
Inte
gra
l
6.0
462
3.0
183
2.9
953
2.9
728
2.5
882
2.5
657
2.5
427
2.5
121
2.5
060
2.5
000
2.4
940
(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
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
455
40.2
691
40.0
000
39.7
164
39.4
400
39.1
636
35.3
598
32.0
070
(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
000
2.1
584
2.1
068
2.1
062
Inte
gra
l
6.0
112
3.3
262
2.8
358
2.8
112
2.7
854
2.5
055
2.5
000
2.4
940
2.3
515
2.3
269
2.3
028
1.7
922
1.7
675
1.7
423
1.7
171
1.6
930
-0.0
015
-0.0
026
(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
O
O
2c
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
7
2c
17
4.2
67
0
16
7.8
59
4
13
6.6
29
1
40
.55
27
40
.27
64
40
.00
00
39
.72
36
39
.44
00
38
.83
63
30
.92
33
23
.02
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
2d
1.1
74
6
2.0
00
0
2.2
25
6
1.9
94
3
Inte
gra
l
8.6
78
78
.66
00
8.6
40
9
6.0
33
1
3.8
69
63
.85
05
3.6
12
7
2.5
04
92
.50
00
2.4
94
5
(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
fe10shy3.1 (1095)
N
O
O
2d
HN
O
COOH
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
9
2d
171.3
214
167.8
012
166.8
776
136.6
001
41.2
510
40.8
291
40.5
527
40.2
764
40.0
000
39.7
164
39.4
400
39.1
563
(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
2.0
00
0
1.0
97
2
2.1
41
6
2.2
06
8
1.1
16
6
4.2
53
2
1.1
89
9
Inte
gra
l
6.0
44
1
2.9
56
82
.94
65
2.5
00
0
1.8
73
21
.69
76
1.5
84
01
.55
30
1.2
88
41
.26
22
1.2
39
21
.21
22
1.1
82
01
.08
82
1.0
58
0
(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
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
158
136.6
291
49.8
186
40.5
527
40.2
764
40.0
000
39.7
164
39.4
400
30.8
651
25.0
394
24.2
103
(ppm)
102030405060708090100110120130140150160170180190
ju25yge.5 1025
N
O
O
2e
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
12
3a.
0.9
85
1
1.0
00
0
1.0
54
3
2.3
63
8
Inte
gra
l
7.0
36
1
3.7
54
43
.74
06
3.7
26
7
3.3
10
6
3.0
54
73
.04
09
3.0
27
0
2.7
90
0
2.5
03
82
.50
00
2.4
96
2
(ppm)
1.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.8
sg1005shy2.5 (1069-2) (b-ala)
3a
N
O
O
O
O
N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
13
3a
17
0.9
97
81
70
.40
75
16
7.2
01
1
13
5.1
29
4
40
.16
76
40
.00
00
39
.83
97
33
.16
44
29
.48
43
25
.86
98
(ppm)
1520253035404550556065707580859095100105110115120125130135140145150155160165170175
sg1005shy2.6 (1069-2)
3a
N
O
O
O
O
N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
14
3b
1.7
25
9
2.0
00
0
2.1
79
5
3.9
44
6
2.4
09
3
1.9
88
8
Inte
gra
l
6.9
91
3
3.5
02
93
.48
90
3.4
75
2
3.3
05
0
2.8
90
22
.80
44
2.7
31
32
.71
62
2.7
01
1
2.5
04
42
.50
06
2.4
96
8
1.8
74
01
.86
02
1.8
45
01
.83
12
1.8
16
0
(ppm)
0.20.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.4
1H AMX500 mh0211 sh3b 1
N
O
O
3b
O
O
N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
15
3b
17
2.0
33
51
71
.08
61
16
9.5
26
6
13
5.4
50
8
41
.00
64
40
.83
88
40
.76
60
40
.67
85
40
.51
09
40
.34
33
40
.17
57
40
.00
81
37
.10
04
28
.66
89
26
.38
80
24
.18
72
(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175
13C AMX500 mh0211 sh3b 2
N
O
O
3b
O
O
N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
16
3c
1.8
329
2.0
000
3.7
729
1.8
978
2.2
028
2.1
952
2.0
860
Inte
gra
l
7.2
607
6.6
681
3.5
239
3.5
100
3.4
962
2.8
103
2.5
960
2.5
809
2.5
670
1.7
866
1.7
715
1.7
563
1.7
400
1.7
261
1.6
870
1.6
454
1.6
303
1.6
164
1.6
013
1.5
861
1.4
235
1.4
122
1.4
071
1.3
983
1.3
920
1.3
870
1.3
806
1.3
769
1.3
617
(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
866
1.7
715
1.7
563
1.7
400
1.7
261
1.6
870
1.6
454
1.6
303
1.6
164
1.6
013
1.5
861
1.4
235
1.4
122
1.4
071
1.3
983
1.3
920
1.3
870
1.3
806
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
3c
17
0.7
63
01
69
.06
50
16
8.3
21
7
13
4.0
12
7
77
.25
87
77
.00
36
76
.74
86
37
.39
68
30
.71
42
27
.96
69
25
.76
61
25
.54
02
24
.00
99
(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175
13C AMX500 mh0210_5135 sh6c 4
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
18
3d
2.1
117
2.0
944
2.0
000
4.1
777
Inte
gra
l
8.2
426
8.2
360
8.2
196
8.2
130
7.7
161
7.7
101
7.6
936
7.6
871
7.2
619
3.3
284
2.9
081
2.5
060
2.5
000
2.4
940
(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
ja29shy.1 2-131
N
O
O
3d
O
O N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
19
3d
17
0.7
54
11
69
.79
40
16
1.7
21
0
13
8.3
38
31
35
.50
18
13
1.2
68
9
12
6.9
27
0
12
3.2
68
6
40
.56
00
40
.28
36
40
.00
00
39
.72
36
39
.44
72
26
.04
31
(ppm)
102030405060708090100110120130140150160170180190
ja29shy.2 2-131
N
O
O
3d
O
O N
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
20
1.0
000
1.0
461
0.9
785
0.9
631
0.4
736
0.4
640
6.3
010
2.4
251
0.9
012
0.8
150
In
teg
ral
7.4
101
7.3
805
7.2
600
6.6
327
6.6
239
6.6
026
6.5
944
6.5
105
6.5
023
6.0
476
5.9
660
5.9
627
4.2
085
4.1
844
4.1
608
4.1
367
3.6
639
3.0
443
2.3
436
2.3
403
1.7
075
1.2
654
1.2
419
1.2
177
(ppm)
0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
1H normal range AV300 fe06nmh1103-5
7.4
101
7.3
805
7.2
600
6.6
327
6.6
239
6.6
026
6.5
944
6.5
105
6.5
023
6.0
476
5.9
660
5.9
627
(ppm)
5.86.06.26.46.66.87.07.27.47.6
O ON
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
21
169.0
095
161.6
420
155.8
381
152.8
635
148.3
906
125.1
897
110.5
419
108.8
982
108.3
818
98.1
996
77.4
206
76.9
988
76.5
696
61.4
709
39.9
792
38.1
173
14.0
000
(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175180185190195
fe171103-5 13C
O ON
O
O
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
22
4
0.97
43
1.00
00
0.91
34
0.81
24
2.02
14
6.17
99
Inte
gral
7.56
617.
5360
6.80
576.
7969
6.77
566.
7668
6.58
496.
5762
6.08
04
3.81
173.
8095
3.35
103.
3455
3.34
003.
3345
3.32
903.
0946
(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 Water suppression fe08nmh1101
7.56
617.
5360
6.80
576.
7969
6.77
566.
7668
6.58
496.
5762
6.08
04
(ppm)
6.06.26.46.66.87.07.27.47.6
O ON
OH
O
4
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
23
4
170.7
631
160.6
682
155.4
026
152.7
988
150.1
878
125.9
542
109.5
826
109.0
954
108.0
917
97.4
367
40.3
291
40.0
528
39.7
764
39.6
818
39.5
000
39.2
236
38.9
400
38.6
636
37.2
454
(ppm)102030405060708090100110120130140150160170
13C Standard AV300 mun hong c13 nmh1109
40.3
291
40.0
528
39.7
764
39.6
818
39.5
000
39.2
236
38.9
400
38.6
636
37.2
454
(ppm)37.538.038.539.039.540.040.5
O ON
OH
O
4
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
24
5
0.9
882
1.0
000
2.0
635
1.1
569
0.9
368
2.0
797
4.3
251
2.1
866
2.4
004
2.1
131
2.3
862
7.1
243
10.0
32
Inte
gra
l
8.2
855
8.2
741
8.2
628
7.5
543
7.5
354
6.7
360
6.7
222
6.7
171
6.7
045
6.6
995
6.5
495
6.5
444
5.9
973
3.6
082
3.4
922
3.4
304
3.4
191
3.4
077
3.3
838
3.3
712
3.3
586
3.3
069
3.2
438
3.2
325
3.2
211
3.2
098
3.0
774
3.0
648
3.0
535
3.0
409
3.0
144
2.5
038
2.5
000
2.4
962
1.3
641
(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
sg06261005.1
O ON
NH
ONHBoc
O
5
2
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
25
5
168.
3598
161.
1307
156.
0368
155.
8255
153.
2530
151.
7883
126.
4574
109.
7547
109.
4341
108.
6689
97.9
273
78.0
401
70.0
021
69.9
074
69.6
377
69.4
191
40.5
903
40.4
227
40.3
352
40.2
551
40.1
676
40.0
000
39.8
324
39.6
648
39.3
150
39.1
765
28.6
754
(ppm)
5101520253035404550556065707580859095100105110115120125130135140145150155160165170175180185190195
sg06261005.2
O ON
NH
ONHBoc
O
5
2
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
26
6
0.9
85
2
0.9
52
1
1.0
00
0
2.0
12
5
1.0
36
2
1.0
07
7
0.9
55
9
4.3
11
7
4.2
20
2
2.1
81
2
2.9
14
8
2.0
64
9
2.0
95
4
6.4
05
7
2.0
10
3
Inte
gra
l
8.3
03
18
.29
18
8.2
80
4
8.0
15
78
.00
56
7.9
94
3
7.5
48
07
.52
90
7.0
09
66
.98
57
6.7
14
66
.70
96
6.6
97
06
.69
19
6.5
40
66
.53
56
5.9
96
0
3.6
06
93
.60
06
3.5
86
73
.57
16
3.4
89
73
.42
92
3.4
17
83
.40
65
3.3
71
23
.35
86
3.3
43
43
.24
64
3.2
35
03
.22
37
3.2
12
33
.16
57
3.1
54
33
.14
17
3.1
30
43
.00
93
2.5
03
82
.50
00
2.4
96
22
.34
11
2.3
26
02
.31
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
![3D Coumarin Systems Based on [2.2]Paracyclophane Synthesis](https://img.dokumen.tips/doc/110x75/617bd62db04f62341e536942/3d-coumarin-systems-based-on-22paracyclophane-synthesis-.jpg)
