Malgorzata Korycka-Machala, Marcin Nowosielski, Aneta Kuron, Sebastian Rykowski, Agnieszka Olejniczak, Marcin Hoffmann and Jaroslaw Dziadek
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- Σόλων Κοτζιάς
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1 Molecules 2017, 21, 154; doi: /molecules Supplementary Materials: Naphthalimides Selectively Inhibit the Activity of Bacterial, Replicative DNA Ligases and Display Bactericidal Effect against Tubercle Bacilli Malgorzata Korycka-Machala, Marcin Nowosielski, Aneta Kuron, Sebastian Rykowski, Agnieszka Olejniczak, Marcin Hoffmann and Jaroslaw Dziadek S1 of S19 Figure S1. Efficiency of a double-stranded DNA 40-bp ligation by M. tuberculosis LigA. SNaP-Shot analysis on Genetic Analyzer 3500.
2 S2 of S19 Figure S2. DNA (40-bp) ligation efficiency as a function of the M. tuberculosis ligase A concentration. Figure S3. DNA (40-bp) ligation efficiency as a function of time (M. tuberculosis, 8.7 ng/µl). Figure S4. DNA (40-bp) ligation efficiency at different temperatures (M. tuberculosis, 8.7 ng/µl).
3 S3 of S19 Figure S5. ESI spectrum of pinafide. ESI-MS: m/z 340 [M + 1] +, calcd. for C18H17N3O4: Figure S6. 1 H-NMR spectrum of pinafide. 1 H-NMR (DMSO): δ (ppm) = 9.46 (d, 1H, H-4), 8.95 (d, 1H, H-6), 8.77 (dd, 1H, H-9), 8.67 (dd, 1H, H-8), 8.05 (q, 1H, H-7), 4.19 (t, 2H, H-2), 2.70 (t, 2H, H-1), (m, 4H, pyrrolidine, overlapping with DMSO), (m, 4H, pyrrolidine). N O N O NO 2 Figure S7. ESI spectrum of mitonafide. ESI-MS: m/z 314 [M + 1] +, calcd. for C16H15N3O4:
4 S4 of S19 Figure S8. 1 H-NMR spectrum of mitonafide. 1 H-NMR (DMSO): δ (ppm) = 9.74 (d, 1H, H-4), 9.23 (d, 1H, H-6), 9.05 (dd, 1H, H-9), 8.95 (dd, 1H, H-8), 8.33 (t, 1H, H-7), 4.45 (t, 2H, H-2), (m, 8H, H-1, N-CH3, N-CH3). Electronic Supporting Information 1 H-NMR spectrum was recorded on a Bruker Avance 600 MHz spectrometer equipped with a TBI probe. The spectrum for 1 H nuclei was recorded at MHz. For NMR, the following solvent was used: DMSO-d6 (δh = 2.50 ppm). All chemical shifts (δ) are quoted in parts per million (ppm). The following abbreviations were used to denote the multiplicities: d = doublet, dd = doublet of doublets, t = triplet, q = quartet, and m = multiplet. Mass spectra were recorded on a CombiFlash PurIon Model Eurus35 (Teledyne ISCO, Lincoln, NE, USA). The ionization was achieved by electrospray ionization in the positive ion mode (ESI+) and negative ion mode (ESI ). The capillary voltage was set to 3.5 kv. The source temperature was 200 C, and the desolvation temperature was 200 C. Nitrogen was used as a desolvation gas (flow 35 L/min, purity >99%). The theoretical molecular masses of the compounds were calculated using the Show Analysis Window option in the ChemDraw Ultra 12.0 program. The calculated m/z corresponds to the average mass of the compounds consisting of natural isotopes. Table S1. In vitro inhibition of DNA LigA by compound NSC Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control)
5 Table S2. In vitro inhibition of DNA LigA by compound NSC S5 of S19 Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S3. In vitro inhibition of DNA LigA by compound NSC5856. Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S4. In vitro inhibition of DNA LigA by compound NSC Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S5. In vitro inhibition of DNA LigA by compound NSC Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S6. In vitro inhibition of DNA LigA by compound NSC Conc. (µm) Ligation (%) E. coli M. tuberculosis T4 0 (control)
6 Table S7. In vitro inhibition of DNA LigA by compound NSC S6 of S19 Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S8. In vitro inhibition of DNA LigA by compound NSC Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S9. In vitro inhibition of DNA LigA by mitonafide. Conc. (µm) E. coli Ligation (%) M. tuberculosis T4 0 (control) Table S10. Results of docking to the open enzyme structure (PDB: 1ZAU). Lp. NCI ZINC Docking ( Open ) (K2) (M2) (M2) (V1) (N1) (N1) (Z1) (G3) (G3) (Q1) (Q1) O2) (O2) Table S dock. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) LYS 123 6,499, ,107, ,391, ALA 128 6,043, , ,391, ALA 322 6,043, , ,391, ARG 182 6,786, ,395, ,391, ARG 211 6,786, ,395, ,391, ASN 209 6,486, ,094, ,391, ASP 125 6,537, ,145, ,391, ASP 291 6,537, ,145, ,391, ASP 295 6,537, ,145, ,391, CYS 235 7,089, ,697, ,391,
7 GLU 121 6,640, ,248, ,391, GLU 184 6,640, ,248, ,391, GLU 265 6,625, ,245, ,380, GLU 293 6,640, ,248, ,391, GLY 126 5,940, , ,391, GLY 183 5,940, , ,391, GLY 296 5,940, , ,391, HSD 236 6,634, ,242, ,391, HSD 266 6,634, ,242, ,391, HSD 292 6,634, ,242, ,391, ILE 124 6,352, , ,391, ILE 234 6,353, , ,391, ILE 294 6,353, , ,391, S7 of S19 Table S min. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) ALA 128 6,044, , ,392, ALA 322 6,044, , ,392, ARG 144 6,787, ,395, ,392, ARG 182 6,771, ,391, ,380, ARG 211 6,787, ,395, ,392, ASN 209 6,486, ,094, ,392, ASP 125 6,537, ,145, ,392, ASP 291 6,537, ,145, ,392, ASP 295 6,537, ,145, ,392, CYS 235 7,089, ,697, ,392, GLU 121 6,640, ,248, ,392, GLU 184 6,640, ,248, ,392, GLU 265 6,640, ,248, ,392, GLU 293 6,640, ,248, ,392, GLY 126 5,940, , ,392, GLY 183 5,940, , ,392, HSD 236 6,634, ,242, ,392, HSD 266 6,634, ,242, ,392, HSD 292 6,634, ,242, ,392, ILE 124 6,353, , ,392, ILE 234 6,353, , ,392, ILE 294 6,353, , ,392, ILE 321 6,353, , ,392, Table S dock. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) ASP 93 5,159, ,145, ,013, HSD 292 5,256, ,242, ,013, LYS 324 5,121, ,107, ,013, ALA 128 4,665, , ,013, ALA 322 4,665, , ,013, ARG 144 5,408, ,395, ,013, ARG 182 5,408, ,395, ,013, ASN 94 5,108, ,094, ,013, ASP 125 5,159, ,145, ,013, ASP 291 5,159, ,145, ,013, ILE 234 4,975, , ,013,
8 ILE 294 4,975, , ,013, LEU 122 4,975, , ,013, LEU 90 4,975, , ,013, LEU 92 4,975, , ,013, LYS 123 5,121, ,107, ,013, LYS 300 5,121, ,107, ,013, MET 89 5,917, ,903, ,013, SER 264 4,863, , ,013, SER 91 4,863, , ,013, TYR 253 5,469, ,455, ,013, VAL 263 4,872, , ,013, VAL 290 4,871, , ,013, S8 of S19 Table S14. 4,783,229 min. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mo) GLU 184 5,262, ,248, ,014, ALA 128 4,666, , ,014, ALA 322 4,666, , ,014, ARG 144 5,409, ,395, ,014, ARG 182 5,409, ,395, ,014, ASN 94 5,108, ,094, ,014, ASP 125 5,159, ,145, ,014, ASP 291 5,159, ,145, ,014, ASP 93 5,159, ,145, ,014, CYS 235 5,711, ,697, ,014, GLU 121 5,262, ,248, ,014, LEU 122 4,975, , ,014, LEU 90 4,975, , ,014, LEU 92 4,975, , ,014, LYS 123 5,121, ,107, ,014, LYS 300 5,121, ,107, ,014, MET 89 5,917, ,903, ,014, PRO 262 4,869, , ,014, SER 264 4,863, , ,014, SER 91 4,863, , ,014, TYR 253 5,469, ,455, ,014, VAL 263 4,872, , ,014, VAL 290 4,872, , ,014, Table S dock Amino Acid Etotal (kj/mo)] EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) GLY 239 4,768, , ,219, ALA 247 4,871, , ,219, ALA 252 4,871, , ,219, ALA 316 4,871, , ,219, ARG 182 5,614, ,395, ,219, ARG 245 5,614, ,395, ,219, ARG 308 5,614, ,395, ,219, ARG 309 5,614, ,395, ,219, ARG 318 5,614, ,395, ,219, ASP 302 5,364, ,145, ,219, GLN 251 5,417, ,197, ,219, GLN 307 5,417, ,197, ,219, GLU 180 5,468, ,248, ,219, GLU 242 5,468, ,248, ,219, GLU 87 5,468, ,248, ,219,
9 GLY 237 4,768, , ,219, GLY 243 4,768, , ,219, GLY 311 4,768, , ,219, HSD 240 5,462, ,242, ,219, HSD 250 5,462, ,242, ,219, LEU 238 5,181, , ,219, LEU 249 5,180, , ,219, LEU 310 5,181, , ,219, S9 of S19 Table S min. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) ARG 88 5,615, ,395, ,219, ALA 252 4,871, , ,219, ALA 316 4,871, , ,219, ARG 182 5,615, ,395, ,219, ARG 245 5,615, ,395, ,219, ARG 308 5,615, ,395, ,219, ARG 318 5,615, ,395, ,219, LEU 238 5,181, , ,219, LEU 249 5,181, , ,219, LEU 310 5,181, , ,219, LEU 86 5,181, , ,219, LEU 90 5,181, , ,219, LYS 300 5,327, ,107, ,219, PHE 244 5,478, ,258, ,219, PRO 246 5,075, , ,219, PRO 317 5,075, , ,219, SER 312 5,069, , ,219, THR 248 5,172, , ,219, THR 313 5,172, , ,219, TRP 319 5,823, ,603, ,219, TYR 253 5,675, ,455, ,219, VAL 241 5,078, , ,219, VAL 304 5,078, , ,219, Table S dock. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) GLN 307 5,417, ,197, ,219, LEU 238 5,180, , ,219, ALA 252 4,871, , ,219, ALA 305 4,871, , ,219, ALA 320 4,871, , ,219, ARG 182 5,614, ,395, ,219, ARG 245 5,614, ,395, ,219, ARG 308 5,614, ,395, ,219, ARG 309 5,614, ,395, ,219, ARG 318 5,614, ,395, ,219, ASP 302 5,364, ,145, ,219, LEU 249 5,162, , ,208, v.h. LEU 256 5,180, , ,219, LEU 306 5,180, , ,219, LEU 310 5,181, , ,219, LEU 90 5,180, , ,219, LYS 300 5,327, ,107, ,219, PHE 244 5,477, ,258, ,219, PRO 246 5,074, , ,219, PRO 317 5,073, , ,219,
10 SER 312 5,068, , ,219, THR 248 5,172, , ,219, TRP 319 5,823, ,603, ,219, S10 of S19 Table S min. ALA 247 4,871, ,52, ,219, ALA 252 4,871, , ,219, ALA 305 4,871, , ,219, ARG 182 5,615, ,395, ,219, ARG 245 5,615, ,395, ,219, ARG 308 5,615, ,395, ,219, ARG 309 5,615, ,395, ,219, ARG 88 5,615, ,395, ,219, GLN 307 5,417, ,197, ,219, GLU 121 5,468, ,248, ,219, LEU 249 5,181, , ,219, LEU 256 5,181, , ,219, LEU 306 5,181, , ,219, LEU 310 5,181, , ,219, LEU 90 5,181, , ,219, LEU 92 5,181, , ,219, LYS 300 5,327, ,107, ,219, MET 89 6,123, ,903, ,219, PRO 246 5,075, , ,219, PRO 317 5,075, , ,219, SER 312 5,069, , ,219, THR 248 5,172, , ,219, TRP 319 5,823, ,603, ,219, Table S dock. GLY 296 4,504, , ,955, ALA 128 4,607, , ,955, ALA 322 4,607, , ,955, ARG 144 5,350, ,395, ,955, ARG 182 5,350, ,395, ,955, ARG 211 5,350, ,395, ,955, ASP 125 5,100, ,145, ,955, ASP 295 5,100, ,145, ,955, GLU 121 5,204, ,248, ,955, GLU 184 5,204, ,248, ,955, GLU 265 5,204, ,248, ,955, GLU 293 5,204, ,248, ,955, GLY 126 4,504, , ,955, GLY 183 4,504, , ,955, GLY 237 4,504, , ,955, HSD 236 5,198, ,242, ,955, HSD 292 5,198, ,242, ,955, ILE 124 4,916, , ,955, ILE 234 4,917, , ,955, ILE 294 4,917, , ,955, LEU 122 4,917, , ,955, LEU 90 4,917, , ,955, LEU 92 4,917, , ,955,
11 Table S min. S11 of S19 GLY 296 4,504, , ,955, ALA 128 4,607, , ,955, ALA 322 4,607, , ,955, ARG 144 5,351, ,395, ,955, ARG 182 5,351, ,395, ,955, ARG 211 5,351, ,395, ,955, ASP 125 5,101, ,145, ,955, ASP 295 5,101, ,145, ,955, CYS 235 5,653, ,697, ,955, GLU 121 5,204, ,248, ,955, GLU 184 5,204, ,248, ,955, GLU 265 5,204, ,248, ,955, GLY 126 4,504, , ,955, GLY 183 4,504, , ,955, GLY 237 4,504, , ,955, HSD 236 5,198, ,242, ,955, ILE 124 4,917, , ,955, ILE 234 4,917, , ,955, LEU 122 4,917, , ,955, LEU 90 4,917, , ,955, LEU 92 4,917, , ,955, LYS 123 5,063, ,107, ,955, LYS 300 5,051, ,104, ,946, Table S dock. LEU 238 4,917, , ,955, ALA 252 4,607, , ,955, ALA 320 4,607, , ,955, ARG 182 5,350, ,395, ,955, ARG 245 5,350, ,395, ,955, ARG 308 5,350, ,395, ,955, ARG 318 5,350, ,395, ,955, GLN 307 5,153, ,197, ,955, GLU 121 5,204, ,248, ,955, LEU 249 4,916, , ,955, LEU 310 4,917, , ,955, LEU 90 4,917, , ,955, LEU 92 4,917, , ,955, LYS 300 5,063, ,107, ,955, PHE 244 5,213, ,258, ,955, PRO 246 4,810, , ,955, PRO 317 4,809, , ,955, SER 312 4,804, , ,955, THR 248 4,908, , ,9555, TRP 319 5,559, ,603, ,955, TYR 253 5,411, ,55, ,955, VAL 241 4,813, , ,955, VAL 298 4,813, , ,955,
12 Table S min. S12 of S19 Amino Acid Etotal (kj/mol) E AA (kj/mol) Eli g (kj/mol) Eint(kJ/mol) ALA 252 4,607, ,52, ,955, ARG 182 5,351, ,395, ,955, ARG 245 5,351, ,395, ,955, ARG 308 5,351, ,395, ,955, GLN 307 5,153, ,197, ,955, GLU 121 5,204, ,248, ,955, GLU 87 5,204, ,248, ,955, GLY 237 4,504, , ,955, GLY 239 4,504, , ,955, GLY 311 4,504, , ,955, HSD 236 5,198, ,242, ,955, HSD 240 5,198, ,242, ,955, LEU 119 4,917, , ,955, LEU 238 4,917, , ,955, LEU 249 4,917, , ,955, LEU 310 4,917, , ,955, LEU 90 4,917, , ,955, LEU 92 4,917, , ,955, LYS 300 5,063, ,107, ,955, PHE 244 5,214, ,258, ,955, PRO 246 4,811, , ,955, PRO 317 4,811, , ,955, SER 312 4,805, , ,955, Table S dock. ALA 247 5,068, , ,416, ALA 252 5,068, , ,416, ARG 182 5,811, ,395, ,416, ARG 245 5,811, ,395, ,416, ARG 308 5,811, ,395, ,416, ASP 302 5,562, ,145, ,416, GLN 251 5,614, ,197, ,416, GLN 307 5,614, ,197, ,416, GLU 121 5,665, ,248, ,416, GLU 265 5,665, ,248, ,416, GLU 87 5,665, ,248, ,416, GLY 237 4,965, ,488, ,416, GLY 239 4,965, ,488, ,416, HSD 236 5,659, ,242, ,416, HSD 240 5,659, ,242, ,416, HSD 250 5,659, ,242, ,416, LEU 119 5,378, , ,416, LEU 238 5,378, , ,416, LEU ,77, , ,416, LEU 90 5,378, , ,416, LYS 300 5,524, ,107, ,416, PHE 244 5,674, ,258, ,416, PRO 246 5,271, , ,416,
13 Table S dock. S13 of S19 ALA 247 5,068, , ,416, ALA 252 5,068, , ,416, ARG 182 5,811, ,395, ,416, ARG 245 5,811, ,395, ,416, ARG 308 5,811, ,395, ,416, ASP 302 5,562, ,145, ,416, GLN 251 5,614, ,197, ,416, GLN 307 5,614, ,197, ,416, GLU 121 5,665, ,248, ,416, GLU 265 5,665, ,248, ,416, GLU 87 5,665, ,248, ,416, GLY 237 4,965, , ,416, GLY 239 4,965, , ,416, HSD 236 5,659, ,242, ,416, HSD 240 5,659, ,242, ,416, HSD 250 5,659, ,242, ,416, LEU 119 5,378, , ,416, LEU 238 5,378, , ,416, LEU 249 5,377, , ,416, LEU 90 5,378, , ,416, LYS 300 5,524, ,107, ,416, PHE 244 5,674, ,258, ,416, PRO 246 5,271, , ,416, Table S min. ALA 252 5,069, , ,416, ARG 182 5,812, ,395, ,416, ARG 245 5,812, ,395, ,416, ARG 308 5,812, ,395, ,416, ASP 302 5,562, ,145, ,416, GLN 307 5,614, ,197, ,416, GLU 121 5,665, ,248, ,416, GLU 87 5,666,046.00,1248, ,416, GLY 237 4,965, , ,416, GLY 239 4,965, , ,416, HSD 236 5,659, ,242, ,416, HSD 240 5,659, ,242, ,416, HSD 250 5,659, ,242, ,416, LEU 238 5,378, , ,416, LEU 249 5,378, , ,416, LEU 90 5,378, , ,416, LEU 92 5,378, , ,416, LYS 300 5,524, ,107, ,416, PHE 244 5,675, ,258, ,416, PRO 246 5,272, , ,416, PRO 317 5,272, , ,416, SER 312 5,266, , ,416, THR 248 5,369, , ,416,
14 Table S dock. S14 of S19 LEU 238 5,378, , ,416, ALA 252 5,068, , ,416, ALA 320 5,068, , ,416, ARG 182 5,811, ,395, ,416, ARG 245 5,811, ,395, ,416, ARG 88 5,811, ,395, ,416, ASP 302 5,562, ,145, ,416, GLN 251 5,614, ,197, ,416, GLN 307 5,614, ,197, ,416, GLU 121 5,665, ,248, ,416, GLU 87 5,665, ,248, ,416, GLY 237 4,965, , ,416, GLY 239 4,965, , ,416, HSD 236 5,659, ,242, ,416, HSD 240 5,659, ,242, ,416, HSD 250 5,659, ,242, ,416, LEU 119 5,378, , ,416, LEU 249 5,378, , ,416, LEU 90 5,378, , ,416, LEU 92 5,378, , ,416, LYS 300 5,524, ,107, ,416, MET 89 6,320, ,903, ,416, PHE 244 5,674, ,258, ,416, Table S min. ALA 252 5,068, , ,416, ALA 320 5,068, , ,416, ARG 182 5,811, ,395, ,416, ARG 245 5,812, ,395, ,416, ARG 308 5,812, ,395, ,416, ARG 88 5,812, ,395, ,416, ASP 302 5,562, ,145, ,416, GLN 307 5,614, ,197, ,416, LEU 90 5,378, , ,416, LEU 92 5,378, , ,416, LYS 300 5,524, ,107, ,416, MET 89 6,322, ,904, ,418, PHE 244 5,675, ,258, ,416, PRO 246 5,272, , ,416, PRO 317 5,272, , ,416, SER 312 5,266, , ,416, SER 91 5,266, , ,416, THR 248 5,369, , ,416, TRP 319 6,020, ,603, ,416, TYR 253 5,872, ,455, ,416, VAL 241 5,275, , ,416, VAL 301 5,275, , ,416, VAL 304 5,275, , ,416,
15 Table S dock. S15 of S19 ALA 128 3,986, , ,333, ALA 320 3,985, , ,333, ALA 322 3,986, , ,333, ARG 144 4,729, ,395, ,333, ARG 182 4,729, ,395, ,333, ARG 211 4,729, ,395, ,333, ASP 125 4,479, ,145, ,333, ASP 295 4,479, ,145, ,333, GLU 121 4,582, ,248, ,333, GLU 184 4,582, ,248, ,333, LEU 122 4,295, , ,333, LEU 129 4,295, , ,333, LEU 90 4,295, , ,333, LEU 92 4,295, , ,333, LYS 123 4,441, ,107, ,333, LYS 300 4,441, ,107, ,333, MET 89 5,237, ,903, ,333, PHE 186 4,592, ,258, ,333, PRO 317 4,188, , ,333, SER 130 4,183, , ,333, SER 264 4,183, , ,333, SER 91 4,183, , ,333, TYR 253 4,789, ,455, ,333, Table S min. GLU 121 4,582, ,248, ,334, ILE 234 4,295, , ,334, ALA 128 3,986, , ,334, ALA 320 3,986, , ,334, ALA 322 3,986, , ,334, ARG 144 4,729, ,395, ,334, ARG 182 4,729, ,395, ,334, ASN 94 4,428, ,094, ,334, ASP 125 4,479, ,145, ,334, CYS 235 5,031, ,697, ,334, LEU 122 4,295, , ,334, LEU 129 4,295, , ,334, LEU 90 4,295, , ,334, LEU 92 4,295, , ,334, LYS 123 4,441, ,107, ,334, LYS 300 4,441, ,107, ,334, MET 89 5,237, ,903, ,334, SER 264 4,183, , ,334, SER 91 4,183, , ,334, TYR 253 4,789, ,455, ,334, VAL 298 4,192, ,583, ,334, GLU 184 4,582, ,248, ,334, GLU 265 4,582, ,248, ,334,
16 Table S dock. S16 of S19 LEU 122 4,295, , ,333, ALA 128 3,985, , ,333, ARG 144 4,729, ,395, ,333, ARG 182 4,729, ,395, ,333, ARG 211 4,729, ,395, ,333, ASP 125 4,479, ,145, ,333, ASP 295 4,479, ,145, ,333, GLU 121 4,582, ,248, ,333, GLU 184 4,582, ,248, ,333, GLU 265 4,582, ,248, ,333, GLY 126 3,882, , ,333, GLY 183 3,882, , ,333, GLY 237 3,882, , ,333, HSD 236 4,576, ,242, ,333, HSD 292 4,576, ,242, ,333, ILE 124 4,294, , ,333, ILE 234 4,295, , ,333, LEU 90 4,295, , ,333, LEU 92 4,295, , ,333, LYS 123 4,441, ,107, ,333, LYS 300 4,441, ,107, ,333, MET 233 5,237, ,903, ,333, MET 89 5,237, ,903, ,333, MET 233 5,237, ,903, ,333, MET 89 5,237, ,903, ,333, Table S min. ILE 234 4,295, , ,334, ALA 128 3,986, , ,334, ALA 322 3,986, , ,334, ARG 144 4,729, ,395, ,334, ARG 182 4,729, ,395, ,334, ARG 211 4,729, ,395, ,334, ASP 125 4,479, ,145, ,334, ASP 295 4,479, ,145, ,334, CYS 235 5,031, ,697, ,334, GLU 121 4,582, ,248, ,334, GLU 184 4,582, ,248, ,334, GLU 265 4,582, ,248, ,334, GLY 126 3,883, , ,334, GLY 183 3,883, , ,334, GLY 237 3,883, , ,334, HSD 236 4,576, ,242, ,334, ILE 124 4,295, , ,334, LEU 122 4,295, , ,334, LEU 90 4,295, , ,334, LEU 92 4,295, , ,334, LYS 123 4,441, ,107, ,334, LYS 300 4,441, ,107, ,334, MET 89 5,237, ,903, ,334,
17 Table S dock. S17 of S19 LEU 238 4,009, , ,048, ALA 252 3,700, , ,048, ALA 320 3,700, , ,048, ARG 182 4,443, ,395, ,048, ARG 308 4,443, ,395, ,048, GLN 307 4,246, ,197, ,048, GLU 121 4,296, ,248, ,048, GLU 265 4,296, ,248, ,048, GLU 87 4,297, ,248, ,048, GLY 237 3,597, , ,048, GLY 239 3,597, , ,048, HSD 236 4,290, ,242, ,048, HSD 240 4,290, ,242, ,048, HSD 250 4,290, ,242, ,048, LEU 119 4,009, , ,048, LEU 249 4,009, , ,048, LEU 256 4,009, , ,048, LEU 90 4,009, , ,048, LEU 92 4,009, , ,048, LYS 300 4,155, ,107, ,048, PRO 246 3,902, , ,048, PRO 317 3,902, , ,048, THR 248 4,000, , ,048, Table S min. LEU 238 4,010, , ,048, ALA 252 3,700, , ,048, ARG 182 4,443, ,395, ,048, ARG 308 4,443, ,395, ,048, CYS 235 4,745, ,697, ,048, GLN 307 4,246, ,197, ,048, GLU 121 4,297, ,248, ,048, GLU 87 4,297, ,248, ,048, GLY 237 3,597, , ,048, GLY 239 3,597, , ,048, HSD 236 4,291, ,242, ,048, HSD 240 4,291, ,242, ,048, HSD 250 4,291, ,242, ,048, LEU 119 4,010, , ,048, LEU 249 4,010, , ,048, LEU 256 4,010, , ,048, LEU 92 4,010, , ,048, LYS 300 4,156, ,107, ,048, PRO 246 3,903, , ,048, PRO 317 3,903, , ,048, THR 248 4,001, , ,048, TRP 319 4,652, ,603, ,048, TYR 253 4,504, ,455, ,048,
18 Table S dock. S18 of S19 ALA 247 5,667, , ,015, ALA 252 5,667, , ,015, ARG 182 6,410, ,395, ,015, ARG 245 6,410, ,395, ,015, ARG 308 6,410, ,395, ,015, ARG 309 6,410, ,395, ,015, ARG 318 6,410, ,395, ,015, ARG 88 6,410, ,395, ,015, LEU 238 5,976, , ,015, LEU 249 5,976, , ,015, LEU 306 5,976, , ,015, LEU 310 5,976, , ,015, LEU 90 5,976, , ,015, LYS 300 6,122, ,107, ,015, MET 89 6,918, ,903, ,015, PHE 244 6,273, ,258, ,015, PRO 246 5,869, , ,015, PRO 317 5,869, , ,015, SER 312 5,864, , ,015, THR 248 5,967, , ,015, TRP 319 6,618, ,603, ,015, TYR 253 6,470, ,455, ,015, VAL 241 5,873, , ,015, Table S min. Amino Acid Etotal (kj/mol) EAA (kj/mol) Eli g (kj/mol) Eint (kj/mol) ALA 252 5,667, , ,015, ARG 182 6,410, ,395, ,015, ARG 245 6,410, ,395, ,015, ARG 308 6,410, ,395, ,015, ARG 309 6,410, ,395, ,015, ARG 88 6,410, ,395, ,015, ASP 302 6,160, ,145, ,015, GLN 307 6,213, ,197, ,015, GLU 242 6,264, ,248, ,015, GLU 87 6,264, ,248, ,015, GLY 237 5,564, , ,015, GLY 239 5,564, , ,015, GLY 311 5,564, , ,015, HSD 236 6,258, ,242, ,015, HSD 240 6,258, ,242, ,015, LEU 238 5,977, , ,015, LEU 249 5,977, , ,015, LEU 310 5,977, , ,015, LEU 90 5,977, , ,015, LYS 300 6,123, ,107, ,015, MET 89 6,919, ,903, ,015, PRO 246 5,870, , ,015, PRO 317 5,870, , ,015,
19 Table S dock. S19 of S19 ALA 247 5,667, , ,015, ALA 252 5,667, , ,015, ARG 182 6,410, ,395, ,015, ARG 245 6,410, ,395, ,015, ARG 308 6,410, ,395, ,015, ARG 309 6,410, ,395, ,015, ARG 318 6,410, ,395, ,015, ARG 88 6,410, ,395, ,015, HSD 250 6,257, ,242, ,015, LEU 238 5,976, , ,015, LEU 249 5,976, , ,015, LEU 306 5,976, , ,015, LEU 310 5,976, , ,015, LEU 90 5,976, , ,015, LYS 300 6,122, ,107, ,015, MET 89 6,918, ,903, ,015, PHE 244 6,273, ,258, ,015, ASP 302 6,160, ,145, ,015, GLN 307 6,213, ,197, ,015, GLU 242 6,263, ,248, ,015, GLU 87 6,263, ,248, ,015, GLY 237 5,564, , ,015, GLY 239 5,564, , ,015,
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