C-Terminal Functionalization of Nylon-3 Polymers: Effects of C-Terminal Groups on Antibacterial and. Hemolytic Activities
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1 C-Terminal Functionalization of Nylon-3 Polymers: Effects of C-Terminal Groups on Antibacterial and Hemolytic Activities Supporting Information Part 2 MALDI-TF, GPC, 1 H NMR, Bioassay and CAC data Jihua Zhang, Matthew J. Markiewicz, Brendan P. Mowery, Bernard Weisblum, Shannon S. Stahl * and Samuel H. Gellman * Department of Chemistry and Department of Pharmacology, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin S2-1
2 1 MALDI-TF data samples generated during efforts to achieve C-terminal functionalization of poly(c) MALDI-TF spectrum of the product from Table S1, entry 1. M refers to poly(c) containing 15 units with an acetyl N-terminus and an imide C-terminus. S2-2
3 MALDI-TF spectrum of the product from Table S1, entry 2. M refers to poly(c) containing 10 subunits with an acetyl N-terminus and an imide C-terminus. Nu = benzylamine. S2-3
4 MALDI-TF spectrum of the product from Table S1, entry 3. M refers to poly(c) containing 12 subunits with an acetyl N-terminus and an imide C-terminus. Nu = benzylamine. S2-4
5 MALDI-TF spectrum of the product from Table S1, entry 4. M refers to poly(c) containing 19 subunits with an acetyl N-terminus and an imide C-terminus. Nu = benzylamine, Nu = benzyl mercaptan. S2-5
6 MALDI-TF spectrum of the product from Table S1, entry 5. M refers to poly(c) containing 9 subunits with an acetyl N-terminus and an imide C-terminus. Nu = benzylamine. S2-6
7 MALDI-TF spectrum of the product from Table S1, entry 6. The labels 1, 2 and 3 indicate [M+Nu+Li] + (2165), [M+Nu+Na] + (2181) and [M+Nu+K] + (2197) peaks, respectively, where M refers to poly(c) containing 13 subunits with an acetyl N-terminus and an imide C-terminus. Nu = benzyl mercaptan. S2-7
8 MALDI-TF spectrum of the product from Table S1, entry 7. M refers to poly(c) containing 23 subunits with an acetyl N-terminus and an imide C-terminus. S2-8
9 MALDI-TF spectrum of the product from Table S1, entry 8. M refers to poly(c) containing 19 subunits with an acetyl N-terminus and an imide C-terminus. S2-9
10 MALDI-TF spectrum of the product from Table S1, entry 10. M refers to poly(c) containing 19 subunits with an acetyl N-terminus and an imide C-terminus. Nu = MeH. S2-10
11 MALDI-TF spectrum of the product from Table S1, entry 11. M refers to poly(c) containing 8 subunits with an acetyl N-terminus and an imide C-terminus. Nu = EtH. S2-11
12 MALDI-TF spectrum of the product from Table S1, entry 12. M refers to poly(c) containing 9 subunits with an acetyl N-terminus and an imide C-terminus. Nu = BnH. S2-12
13 MALDI-TF spectrum of the product from Table S1, entry 13. M refers to poly(c) containing 8 subunits with an acetyl N-terminus and an imide C-terminus. Nu = HCH 2 CH 2 2. S2-13
14 MALDI-TF spectrum of the product from Table S1, entry 14. M refers to poly(c) containing 31 subunits with an acetyl N-terminus and an imide C-terminus. S2-14
15 MALDI-TF spectrum of the product from Table S1, entry 15. M refers to poly(c) containing 10 subunits with an acetyl N-terminus and an imide C-terminus. S2-15
16 MALDI-TF spectrum of the product from Table S1, entry 16. M refers to poly(c) containing 29 subunits with an acetyl N-terminus and an imide C-terminus. S2-16
17 2 GPC, 1 H NMR and MALDI-TF characterization data for C-terminal imide and C- terminal functionalized 37:63 CH:MM nylon-3 random copolymers (R = side chain of either CH or MM) Solvents GPC trace (RI detection) of Boc-protected 1 in THF. M n = 4627, PDI = 1.10, dn/dc = PPM 1 H NMR of 1 in D 2 at 10 mg/ml. S2-17
18 MALDI-TF spectrum of 1. S2-18
19 Solvents GPC trace (RI detection) of Boc-protected 2 in THF. M n = 4749, PDI = 1.13, dn/dc = PPM 1 H NMR of 2 in D 2 at 10 mg/ml. S2-19
20 MALDI-TF spectrum of 2. S2-20
21 Solvents GPC trace (RI detection) of Boc-protected 3 in THF. M n = 5845, PDI = 1.15, dn/dc = N 0.63 n R' + H 3 N PPM 1 H NMR of 3 in D 2 at 10 mg/ml. S2-21
22 MALDI-TF spectrum of 3. S2-22
23 Solvents TrtS N n R' BocHN GPC trace (RI detection) of Boc-protected 4 (with trityl-proteced thiol) in THF. M n = 5337, PDI = 1.07, dn/dc = HS N n R' + H 3 N PPM 1 H NMR of 4 in D 2 at 10 mg/ml. S2-23
24 HS N n R' + H 3 N MALDI-TF spectrum of 4. S2-24
25 N n HN BocHN Solvents GPC trace (RI detection) of Boc-protected 1B-a in THF. M n = 4890, PDI = 1.13, dn/dc = PPM 1 H NMR of 1B-a in D 2 at 10 mg/ml. S2-25
26 MALDI-TF spectrum of 1B-a. S2-26
27 N n HN BocHN Solvents GPC trace (RI detection) of Boc-protected 1B-b in THF. M n = 5975, PDI = 1.07, dn/dc = PPM 1 H NMR of 1B-b in D 2 at 10 mg/ml. S2-27
28 MALDI-TF spectrum of 1B-b. S2-28
29 N n HN BocHN Solvents GPC trace (RI detection) of Boc-protected 2B-a in THF. M n = 3948, PDI = 1.13, dn/dc = N n HN + H 3 N PPM 1 H NMR of 2B-a in D 2 at 10 mg/ml. S2-29
30 N n HN + H 3 N MALDI-TF spectrum of 2B-a. S2-30
31 N n HN BocHN GPC trace (RI detection) of Boc-protected 2B-b in THF. M n = 4837, PDI = 1.12, dn/dc = N n HN + H 3 N PPM 1 H NMR of 2B-b in D 2 at 10 mg/ml. Polymer 2B-b does not produce a MALDI-TF spectrum. S2-31
32 Solvents GPC trace (RI detection) of Boc-protected 3B in THF. M n = 4112, PDI = 1.12, dn/dc = PPM 1 H NMR of 3B in D 2 at 10 mg/ml. S2-32
33 MALDI-TF spectrum of 3B. S2-33
34 Solvents N n HN BocHN GPC trace (RI detection) of Boc-protected 1C-a in THF. M n = 5072, PDI = 1.09, dn/dc = PPM 1 H NMR of 1C-a in D 2 at 10 mg/ml. S2-34
35 MALDI-TF spectrum of 1C-a. S2-35
36 N n HN BocHN GPC trace (RI detection) of Boc-protected 1C-b in THF. M n = 6135, PDI = 1.12, dn/dc = PPM 1 H NMR of 1C-b in D 2 at 10 mg/ml. S2-36
37 MALDI-TF spectrum of 1C-b. S2-37
38 N n HN BocHN Solvents GPC trace (RI detection) of Boc-protected 2D in THF. M n = 5753, PDI = 1.11, dn/dc = PPM 1 H NMR of 1E in D 2 at 10 mg/ml. S2-38
39 MALDI-TF spectrum of 1E. S2-39
40 Solvents GPC trace (RI detection) of Boc-protected 1D-a in THF. M n = 5676, PDI = 1.06, dn/dc = PPM 1 H NMR of 1D-a in D 2 at 10 mg/ml. S2-40
41 MALDI-TF spectrum of 1D-a. S2-41
42 N n HN BocHN GPC trace (RI detection) of Boc-protected 1D-b in THF. M n = 5544, PDI = 1.09, dn/dc = PPM 1 H NMR of 1D-b in D 2 at 10 mg/ml. S2-42
43 MALDI-TF spectrum of 1D-b. S2-43
44 N n HN STrt BocHN Solvents GPC trace (RI detection) of Boc-protected 1F (with trityl-proteced thiol) in THF. M n = 5449, PDI = 1.11, dn/dc = N n HN STrt BocHN PPM 1 H NMR of Boc-protected 1F (with trityl-proteced thiol) in CDCl 3 at 10 mg/ml. S2-44
45 Solvents N n HN STrt BocHN GPC trace (RI detection) of Boc-protected 2F (with trityl-proteced thiol) in THF. M n = 4917, PDI = 1.12, dn/dc = N n HN STrt BocHN PPM 1 H NMR of Boc-protected 2F (with trityl-proteced thiol) in CDCl 3 at 10 mg/ml. S2-45
46 N n HN SH + H 3 N PPM 1 H NMR of 2F D 2 at 10 mg/ml. N n HN SH + H 3 N MALDI-TF spectrum of 2F. S2-46
47 Solvents TrtS N n HN BocHN GPC trace (RI detection) of Boc-protected 4C (with trityl-proteced thiol) in THF. M n = 4573, PDI = 1.13, dn/dc = TrtS N n HN BocHN PPM 1 H NMR of Boc-protected 4C (with trityl-proteced thiol) in CDCl 3 at 10 mg/ml. S2-47
48 PPM 1 H NMR of 4C D 2 at 10 mg/ml. MALDI-TF spectrum of 4C. S2-48
49 3 Antibacterial and hemolytic assays Dose-response curves of antibacterial activity of polymer 1. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of polymer 2. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-49
50 Dose-response curves of antibacterial activity of polymer 3. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of polymer 1B-a. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-50
51 Dose-response curves of antibacterial activity of polymer 1B-b. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of polymer 2B-a. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-51
52 Dose-response curves of antibacterial activity of polymer 2B-b. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of polymer 3B. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-52
53 Dose-response curves of antibacterial activity of 1C-a. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of 1C-b. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. The polymer is not fully soluble in BHI > 100 µg/ml. S2-53
54 Dose-response curves of antibacterial activity of 1D-a. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. Dose-response curves of antibacterial activity of 1D-b. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-54
55 Dose-response curves of antibacterial activity of 1E. Numbers in the parentheses are the MIC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. The polymer is not fully soluble in BHI > 200 µg/ml. S2-55
56 Dose-response curves of hemolytic activity. Numbers in the parentheses are the MHC values (µg/ml) deduced from the corresponding curves. The lines simply connect the data points. S2-56
57 Dose-response curves of hemolytic activity. Numbers in the parentheses are the MHC (µg/ml) values deduced from the corresponding curves. The lines simply connect the data points. S2-57
58 3 CAC measurements in Tris-buffered saline DPH fluorescence plot for the non-aggregating polymers DPH fluorescence plot for 1C-a. CAC = 220 µg/ml. S2-58
59 DPH fluorescence plot for 1C-b. CAC = 70 µg/ml. DPH fluorescence plot for 1E. CAC = 360 µg/ml. S2-59
60 DPH fluorescence plot for DDM. CAC = 0.19 mm (lit. 0.17mM). S2-60
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