10.1071/CH20017 AC Australian Journal of Chemistry 2021 ...1 10.1071/CH20017_AC CSIRO 2021...
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1 10.1071/CH20017_AC CSIRO 2021 Australian Journal of Chemistry 2021, 74(3), 199-203 Supplementary Material Synthesis and Characterization of Photolabile SPhNPPOC-Protected (R)-MiniPEG Containing Chiral γ-Peptide Nucleic Acid Monomers Qingteng Lai, A Bo Dong, A,B Kaixuan Nie, A,B Huanhuan Shi, A,B Bo Liang, C and Zhengchun Liu A,B,D A Hunan Key Laboratory for Super Microstructure and Ultrafast Process, Department of Electronic Information Science and Technology, School of Physics and Electronics, Central South University, Changsha, Hunan 410083, China. B School of Basic Medical Science, Central South University, Changsha, Hunan 410083, China. C State Engineering Laboratory of Highway Maintenance Technology, School of Traffic and Transportation Engineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China. D Corresponding author. Email: [email protected] Content 1. 1 HNMR of SPhNPPOC-Cl ............................................................................................................. 2 2. 1 HNMR of SPhNPPOC-MP-A-OH ................................................................................................ 3 3. 13 CNMR of SPhNPPOC-MP-A-OH............................................................................................... 3 4. ESI-MS of SPhNPPOC-MP-A-OH ................................................................................................ 4 5. 1 HNMR of SPhNPPOC-MP-G-OH ................................................................................................ 4 6. 13 CNMR of SPhNPPOC-MP-G-OH............................................................................................... 5 7. ESI-MS of SPhNPPOC-MP-G-OH ................................................................................................ 5 8. 1 HNMR of SPhNPPOC-MP-C-OH ................................................................................................ 6 9. 13 CNMR of SPhNPPOC-MP-C-OH ............................................................................................... 6 10. ESI-MS of SPhNPPOC-MP-C-OH .............................................................................................. 7 11. 1 HNMR of SPhNPPOC-MP-T-OH ............................................................................................... 7 12. 13 CNMR of SPhNPPOC-MP-T-OH.............................................................................................. 8 13. ESI-MS of SPhNPPOC-MP-T-OH ............................................................................................... 8 14. ESI-MS of photo-deprotected SPhNPPOC-MP-T-OH................................................................. 8
Transcript of 10.1071/CH20017 AC Australian Journal of Chemistry 2021 ...1 10.1071/CH20017_AC CSIRO 2021...
1
10.1071/CH20017_AC
CSIRO 2021
Australian Journal of Chemistry 2021, 74(3), 199-203
Supplementary Material
Synthesis and Characterization of Photolabile SPhNPPOC-Protected (R)-MiniPEG Containing Chiral γ-Peptide Nucleic Acid Monomers
Qingteng Lai,A Bo Dong,A,B Kaixuan Nie,A,B Huanhuan Shi,A,B Bo Liang,C and Zhengchun LiuA,B,D
AHunan Key Laboratory for Super Microstructure and Ultrafast Process, Department of Electronic Information
Science and Technology, School of Physics and Electronics, Central South University, Changsha, Hunan 410083,
China. BSchool of Basic Medical Science, Central South University, Changsha, Hunan 410083, China. CState Engineering Laboratory of Highway Maintenance Technology, School of Traffic and Transportation
Engineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China. DCorresponding author. Email: [email protected]
Content 1. 1HNMR of SPhNPPOC-Cl ............................................................................................................. 2
2. 1HNMR of SPhNPPOC-MP-A-OH ................................................................................................ 3
3. 13CNMR of SPhNPPOC-MP-A-OH ............................................................................................... 3
4. ESI-MS of SPhNPPOC-MP-A-OH ................................................................................................ 4
5. 1HNMR of SPhNPPOC-MP-G-OH ................................................................................................ 4
6. 13CNMR of SPhNPPOC-MP-G-OH ............................................................................................... 5
7. ESI-MS of SPhNPPOC-MP-G-OH ................................................................................................ 5
8. 1HNMR of SPhNPPOC-MP-C-OH ................................................................................................ 6
9. 13CNMR of SPhNPPOC-MP-C-OH ............................................................................................... 6
10. ESI-MS of SPhNPPOC-MP-C-OH .............................................................................................. 7
11. 1HNMR of SPhNPPOC-MP-T-OH ............................................................................................... 7
12. 13CNMR of SPhNPPOC-MP-T-OH.............................................................................................. 8
13. ESI-MS of SPhNPPOC-MP-T-OH ............................................................................................... 8
14. ESI-MS of photo-deprotected SPhNPPOC-MP-T-OH................................................................. 8
2
1. 1HNMR of SPhNPPOC-Cl
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5
f1 (ppm)
0.0E+00
5.0E+07
1.0E+08
1.5E+08
2.0E+08
2.5E+08
3.0E+08
3.5E+08
4.0E+08
4.5E+08
5.0E+08
3.02
3.78
2.35
1.00
2.03
1.09
5.22
1.00
0.98
0.99
1.19
1.21
1.22
2.51
2.72
2.74
2.75
2.77
3.18
3.20
3.21
3.22
3.27
3.28
6.99
7.46
7.47
7.47
7.48
7.48
7.49
7.50
7.75
S O
CH3
CH3
Cl
ON+
O
O-
3
2. 1HNMR of SPhNPPOC-MP-A-OH
3. 13CNMR of SPhNPPOC-MP-A-OH
0102030405060708090100110120130140150160170180ppm
14.1
218
.00
26.0
1
33.4
4
44.5
549
.34
49.8
653
.26
58.4
866
.69
67.5
870
.02
70.2
370
.96
71.6
171
.70
123.
2912
3.33
124.
4812
8.28
128.
4312
8.65
129.
3213
0.55
132.
0313
3.12
133.
2113
5.77
136.
8714
2.17
145.
7814
8.36
149.
7115
1.79
152.
8915
5.95
167.
8817
1.28
NH
N
O
OH
O
S
NO2
O
OO
O
ON
NN
N
HN O
O
171.28167.88
155.95
151.79149.71
152.89
148.36
145.78
142.17
136.87
135.77133.21
133.12 132.03
130.55
130.55129.32
128.43
128.87
128.87
128.43
128.65
128.28
128.28
124.48
123.33
123.29
71.70
71.6170.96 70.23
70.02
67.58
66.69
58.48
53.26
49.86
49.34
44.5533.44
26.01
18.00
14.12
4
4. ESI-MS of SPhNPPOC-MP-A-OH Chemical Formula: C43H50N8O12S Exact Mass: 902.32689 Calcd. [M-H]－: 901.31961 Found: 901.32844
5. 1HNMR of SPhNPPOC-MP-G-OH
5
6. 13CNMR of SPhNPPOC-MP-G-OH
010203040506070809010011012013014015016017080ppm
14.1
217
.97
26.0
2
33.4
3
44.2
444
.40
48.7
049
.81
58.4
867
.58
67.6
567
.84
70.0
270
.25
71.6
171
.70
119.
5311
9.79
124.
4712
8.43
128.
7112
8.94
129.
2313
0.51
132.
2113
2.99
133.
1313
5.66
136.
0014
0.90
142.
0614
7.68
148.
4515
0.06
155.
1815
5.62
155.
9516
7.84
170.
82
7. ESI-MS of SPhNPPOC-MP-G-OH Chemical Formula: C43H50N8O13S Exact Mass: 918.32180 Calcd. [M-H]－: 917.31453 Found: 917.32236
NH
N
O
OH
O
S
NO2
O
OO
O
ONH
NN
N
O
NH
O
O
170.82167.84
155.95
155.62
155.18150.06148.45
147.68
142.06
140.90
136.00135.66133.13
132.99
132.99
132.21130.51
130.51
129.23
128.94
128.94
128.71
128.43
128.43124.47
119.79
119.53
71.70
71.61
70.2570.02
67.84
67.65
67.58
58.48
49.81
48.70
44.40
44.2433.43
26.02
17.97
14.12
6
8. 1HNMR of SPhNPPOC-MP-C-OH
9. 13CNMR of SPhNPPOC-MP-C-OH
010203040506070809010011012013014015016017080ppm
14.1
418
.09
26.0
1
33.4
2
48.2
649
.20
49.8
250
.11
58.4
966
.92
67.5
467
.75
70.0
270
.20
70.8
871
.70
94.2
512
4.51
128.
3912
8.49
128.
6012
8.67
128.
9312
9.30
130.
5613
2.03
133.
1113
3.19
135.
7913
6.45
142.
1214
8.36
151.
3515
3.59
155.
4515
5.91
163.
43
168.
39
NH
N
O
OH
O
S
NO2
O
OO
O
ON
N O
HN O
O
168.39163.43
155.91
155.45
153.59
151.35
148.36
142.12
136.45
135.79
133.19133.11 132.03
130.56
130.56
129.30
128.93
128.93
128.67
128.60
128.60
128.49
128.39
128.39
124.51
94.2571.70
70.8870.20
70.02
67.75
67.54
66.92
58.49
50.11
49.82
49.20
48.26
33.42
26.01
18.09
14.14
7
10. ESI-MS of SPhNPPOC-MP-C-OH Chemical Formula: C42H50N6O13S Exact Mass: 878.31566 Calcd. [M-H]－: 877.30838 Found: 877.31610
11. 1HNMR of SPhNPPOC-MP-T-OH
8
12. 13CNMR of SPhNPPOC-MP-T-OH
010203040506070809010011012013014015016017080ppm
12.3
714
.15
18.0
1
26.0
3
33.4
5
48.1
749
.12
49.8
752
.60
58.5
067
.60
70.0
370
.07
70.2
770
.91
71.7
2
108.
50
124.
5012
8.76
129.
2713
0.54
133.
0413
5.75
142.
0814
2.26
142.
6014
2.72
148.
4215
1.53
155.
9116
4.85
167.
2516
8.51
13. ESI-MS of SPhNPPOC-MP-T-OH Chemical Formula: C35H45N5O12S Exact Mass: 759.27854 Calcd. [M-H]－: 758.27127 Found: 758.27892
14. ESI-MS of photo-deprotected SPhNPPOC-MP-T-OH Chemical Formula: C17H28N4O8 Exact Mass: 416.19071 Calcd1. [M+H]+: 417.197990 Found: 417.19727 Calcd2. [M+K]+: 455.28901 Found: 455.14375
NH
N
O
OH
O
S
NO2
O
OO
O
O
N
NH
O
O
168.51167.25
164.85
155.91
151.53
148.42142.72
142.60
142.26142.08
135.75
133.04
133.54
129.27
128.76
124.50
108.5071.72
70.9170.27
70.07
70.03
67.60
58.50
52.60
49.87
49.12
48.17
33.45
26.03
18.01
14.15
12.37
133.54133.04
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