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1 advances.sciencemag.org/cgi/content/full/3/8/e /dc1 Supplementary Materials for A polyaromatic nanocapsule as a sucrose receptor in water Masahiro Yamashina, Munetaka Akita, Taisuke Hasegawa, Shigehiko Hayashi, Michito Yoshizawa This PDF file includes: Published 25 August 2017, Sci. Adv. 3, e (2017) DOI: /sciadv scheme S1. Host-guest interactions between 1 and 3a. scheme S2. Formation of 1 3b. scheme S3. Host-guest interactions between 1 and 2b. scheme S4. Formation of 1 4a. scheme S5. Selective encapsulation of 4a by 1 from a mixture of 2a and 4a. scheme S6. Competitive binding experiment of 4a and 4b by 1. fig. S1. 1 H NMR spectra (500 MHz, D2O, room temperature) of 1 with various monosaccharides. fig. S2. ESI-TOF MS spectra (H2O, room temperature) of 1 with various monosaccharides. fig. S3. Temperature-dependent 1 H NMR spectra (500 MHz, D2O) of 13b. fig. S4. 1 H DOSY NMR spectrum (500 MHz, D2O, 25 C) of 1 3b. fig. S5. 1D NOESY spectrum (500 MHz, D2O, room temperature, irradiation at 7.96 ppm) of 1 3b. fig. S6. Concentration-dependent 1 H NMR spectra (500 MHz, D2O, room temperature) of 13b. fig. S7. ESI-TOF MS spectrum (H2O, room temperature) of 1 3b at 5.0 μm. fig. S8. ESI-TOF MS spectrum (H2O) of 1 3b. fig. S9. Optimized structure of 1 3b (R = -OCH3). fig. S10. 1 H NMR spectra (500 MHz, D2O, room temperature) of 12a. fig. S11. 1 H NMR spectra (500 MHz, D2O, 60ºC) of 12a.
2 fig. S12. 1 H- 1 H Correlation spectroscopy (COSY) spectra (500 MHz, D2O, room temperature) of 12a. fig. S13. NOESY spectra (500 MHz, D2O, room temperature) of 12a. fig. S14. Homonuclear Hartmann-Hahn (HOHAHA) spectrum (500 MHz, D2O, 60ºC) of 12a. fig. S15. Heteronuclear single quantum coherence (HSQC) NMR spectrum (500 MHz, D2O, 60ºC) of 12a. fig. S16. 1 H DOSY NMR spectrum (500 MHz, D2O, room temperature) of 1 2a. fig. S17. ESI-TOF MS spectrum (H2O, room temperature) of 12a. fig. S18. 1 H NMR spectra (500 MHz, D2O, room temperature) of 1 with various disaccharides. fig. S19. Optimized structure of 1 2a (R = -OCH3). fig. S20. A snapshot of 12a (R = -OCH3) in water from molecular dynamics simulation. fig. S21. Temperature-dependent 1 H NMR spectra (500 MHz, D2O) of 12a. fig. S22. Concentration-dependent 1 H NMR spectra (500 MHz, D2O, mm based on 1, room temperature) of 12a. fig. S23. Selective encapsulation of 2a from a mixture of 2a and 2b by 1. fig. S24. Selective encapsulation of 2a from a mixture of 2a and various disaccharides by 1. fig. S25. Encapsulation of 4a within 1. fig. S26. Encapsulation of 4b within 1. fig. S27. Concentration-dependent 1 H NMR spectra (500 MHz, D2O, 0.8 mm based on 1, room temperature) of 14a and 14b. fig. S28. Competitive binding experiments of 2a and artificial sugars by 1. fig. S29. Competitive binding experiment of 4a and 4b by 1. table S1. Theoretical binding energies of host-guest complexes (R = -OCH3). table S2. Thermodynamic parameters of 1 2a. table S3. Binding constants of 1 toward 2a in water.
3 scheme S1. Host-guest interactions between 1 and 3a. Host-guest interactions between 1 and monosaccharides: Pt-capsule 1 (1.5 mg, 0.39 mol) and D-glucose (3a; 0.4 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. New host-guest complexes and interactions were not observed by 1 H NMR and ESI-TOF MS analyses. Similarly, no interactions were also observed between 1 and other monosaccharides such as D-fructose (3d), D-mannose (3e), and D-galactose (3f), and a mixture of 3a and 3d under the same conditions. On the other hand, methyl -D-glucopyranoside (3c) was encapsulated within 1 in water to give 1:1 host-guest complex 13c in 81% yield based on 1. scheme S2. Formation of 1 3b. Formation of 13b: Pt-capsule 1 (1.5 mg, 0.39 mol) and 2,3,4,6-tetra-O-methyl--D-glucopyranoside (3b; 0.1 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. The quantitative formation of 1:1 host-guest complex 13b was confirmed by NMR and ESI-TOF MS analyses. Observed two sets of the 13b signals indicate the formation of two conformational host-guest isomers. Two sets of the host-guest signals coalesced at 95ºC. Typical 1 H NMR analysis provides a lower limit for the binding constant of capsule 1 toward 3b due to the strong host-guest interactions. The 1 H NMR and ESI-TOF MS spectra of an aqueous solution (5.0 M) of 13b showed no peaks derived from empty 1 (figs. S6 and S7). Therefore, assuming there is less than 2% empty 1 at this concentration ( M), a minimum binding constant (Ka) (= [13b]/[1] [3b] = [ ]/[
4 10 6 ] 2 = ) can be estimated to be approximately >10 8 M 1. 1 H NMR (500 MHz, D2O, r.t.): 0.45 (s, 3b), 0.28 (s, 3b), 0.19 (s, 3b), 0.17 (s, 3b), 0.05 (s, 3b), 0.04 (s, 3b), 0.05 (s, 3b), 0.15 (s, 3b), 0.18 (s, 3b), 0.31 (m, 3b), 0.67 (br, 3b), 0.80 (m, 3b), 0.86 (m, 3b), 0.95 (m, 3b), 1.03 (m, 3b), (s, 24H, 1), 3.10 (m, 16H, 1), (m, 24H, 1), 4.48 (m, 4H, 1), 4.61 (m, 4H, 1), 6.02 (s, 1), 6.11 (s, 1), 6.47 (d, J = 8.5 Hz, 1), 6.58 (br, 1), 6.61 (d, J = 8.5 Hz, 1), 6.74 (br, 1), 6.98 (d, J = 8.5 Hz, 1), 7.09 (br, 1), 7.16 (br, 1), 7.51 (dd, J = 8.5, 7.0 Hz, 1), 7.68 (d, J = 8.5 Hz, 1), 7.76 (dd, J = 8.5, 7.0 Hz, 1), (m, 1), 8.35 (dd, J = 8.0, 5.5 Hz, 1), 8.55 (d, J = 8.0 Hz, 1), 8.59 (d, J = 8.0 Hz, 1), 9.21 (d, J = 5.5 Hz, 1), 9.25 (d, J = 5.5 Hz, 1). 1 H NMR (500 MHz, D2O, 90ºC): 0.31 (s, 3b), 0.10 (s, 3b), 0.01 (s, 3b), 0.12 (s, 3b), 0.27 (s, 3b), 0.44 (br, 3b), 0.75 (br, 3b), 1.15 (br, 3b), 1.67 (br, 3b), 2.64 (s, 24H, 1) 3.17 (br, 16H, 1), (br, 8H, 1), 6.07 (br 4H, 1), 6.61 (br, 8H, 1), 6.74 (br, 8H, 1), 6.94 (br, 8H, 1), 7.20 (br, 8H, 1), 7.55 (br, 8H, 1), 7.71 (br, 8H, 1), 7.82 (br, 8H, 1), 8.00 (br, 8H, 1), 8.45 (br, 8H, 1), 8.61 (br, 8H, 1), 9.28 (br, 8H, 1). IR (KBr, cm 1 ): 3061, 2953, 2925, 2883, 2838, 1637, 1604, 1442, 1382, 1357, 1259, 1195, 1162, 1103, 1066, 1031, 945, 884, 827, 769, 706, 671, 644, H DOSY NMR (500 MHz, D2O, 25ºC): D = m 2 s 1. ESI-TOF MS (H2O): m/z [13b 2 NO3 ] 2+, [13b 3 NO3 ] 3+, [13b 4 NO3 ] 4+. scheme S3. Host-guest interactions between 1 and 2b. Host-guest interactions between 1 and disaccharides: Pt-capsule 1 (1.5 mg, 0.39 mol) and D-trehalose (2b; 0.7 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. New host-guest complexes and interactions were not observed by 1 H NMR analysis. Similarly, no interactions were also observed between 1 and other disaccharides such as D-lactose (2c), D-maltose (2d), D-cellobiose (2e), and lactulose (2f) under the same conditions.
5 scheme S4. Formation of 1 4a. Formation of 14a and 14b: Pt-capsule 1 (1.5 mg, 0.39 mol) and sucralose (4a; 0.8 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. The quantitative formation of 1:1 host-guest complex 14a was confirmed by NMR and ESI-TOF MS analyses. Similarly, aspartame (4b) was also encapsulated within 1 to give 14b under the same conditions. Host-guest structures 14a and 14b are obtained 91% and 82% yields in water upon addition of 1.0 equivalent of the corresponding guests, as confirmed by 1 H NMR analysis. Thus, their binding constants (Ka) (= [14a,b]/[1] [4a,b]) were estimated to and M 1, respectively. 1 H NMR (500 MHz, D2O, r.t.): 0.69 (d, J = 12 Hz, 1H, 4a), 0.28 (d, J = 10 Hz, 2H, 4a), 0.01 (t, J = 9.5 Hz, 1H, 4a), 0.30 (d, J = 13 Hz, 1H, 4a), (m, 2H, 4a), 0.46 (d, J = 10 Hz, 1H, 4a), (m, 2H, 4a), 0.83 (d, J = 10 Hz, 1H, 4a), 1.70 (d, J = 6.5 Hz, 1H, 4a), 1.86 (d, J = 9.5 Hz, 1H, 4a), 2.47 (s, 24H, 1), 2.77 (br, 1H, 4a), (m, 16H, 1), 3.49 (s, 12H, 1), (m, 24H, 1), 4.48 (m, 4H, 1), 4.62 (m, 4H, 1), 6.11 (s, 4H, 1), 6.54 (d, J = 9.0 Hz, 8H, 1), 6.85 (br, 8H, 1), 7.05 (d, J = 9.0 Hz, 8H, 1), 7.32 (br, 8H, 1), 7.55 (dd, J = 9.0, 7.0 Hz, 8H, 1), 7.72 (d, J = 9.0 Hz, 8H, 1), 7.81 (dd, J = 9.0, 7.0 Hz, 8H, 1), 8.04 (d, J = 9.0 Hz, 8H, 1), 8.11 (s, 8H, 1), 8.32 (dd, J = 8.0, 5.5 Hz, 8H, 1), 8.55 (d, J = 8.0 Hz, 8H, 1), 9.21 (d, J = 5.5 Hz, 8H, 1). ESI-TOF MS (H2O): m/z [14a 2 NO3 ] 2+, [14a 3 NO3 ] 3+, [14a 4 NO3 ] H NMR (500 MHz, D2O, r.t.): 1.02 (br, 4b), (m, 4b), (m, 4b), 0.43 (br, 4b), 0.61 (br, 4b), 1.43 (br, 4b), 1.54 (br, 4b), 2.45 (s, 24H, 1), (m, 16H, 1), 3.48 (s, 12H, 1), 3.52 (br, 4b), 3.61 (br, 4b), 3.94 (m, 8H, 1), 3.94 (m, 8H, 1), 4.04 (m, 8H, 1), 4.47 (m, 4H, 1), 4.62 (m, 4H, 1), (s, 4H, 1), (m, 1), 6.71 (br, 1), (m, 1), 7.15 (br, 1), (m, 8H, 1), (m, 16H, 1), (m, 16H, 1), 8.35 (dd, J = 8.0, 5.0 Hz, 8H, 1), 8.56 (d, J = 8.0 Hz, 8H, 1), 9.26 (d, J = 5.0 Hz, 8H, 1).
6 scheme S5. Selective encapsulation of 4a by 1 from a mixture of 2a and 4a. Selective encapsulation experiment: Pt-capsule 1 (1.5 mg, 0.39 mol), D-sucrose (2a; 0.7 mg, 2.0 mol), and sucralose (4a; 0.8 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. The selective formation of 1:1 host-guest complex 14a was confirmed by 1 H NMR analysis. The selective encapsulation of aspartame (4b) within 1 was also observed from a mixture of 2a and 4b under the same conditions. scheme S6. Competitive binding experiment of 4a and 4b by 1. Competitive binding experiment: Pt-capsule 1 (1.5 mg, 0.39 mol), sucralose (4a; 0.8 mg, 2.0 mol), and aspartame (4b; 0.6 mg, 2.0 mol) were added to a glass test tube containing D2O (0.5 ml). The mixture was stirred at 60ºC for 30 min. The formation and ratio of 14a and 14b complexes were confirmed by 1 H NMR analysis.
7 fig. S1. 1 H NMR spectra (500 MHz, D 2O, room temperature) of 1 with various monosaccharides. (A) Capsule 1 and the mixtures of 1 with (B) 3a, (C) 3c, (D) 3d, (E) 3e, (F) 3f, or (G) a mixture of 3a and 3d in D 2O.
8 A B C [M] 4+ [M] 3+ [M] 2+ D E F G m/z fig. S2. ESI-TOF MS spectra (H 2O, room temperature) of 1 with various monosaccharides. (A) Capsule 1 and the mixtures of 1 with (B) 3a, (C) 3c, (D) 3d, (E) 3e, (F) 3f, or (G) a mixture of 3a and 3d in H 2O.
9 fig. S3. Temperature-dependent 1 H NMR spectra (500 MHz, D 2O) of 13b. (A) Room temperature and (B) 90ºC.
10 fig. S4. 1 H DOSY NMR spectrum (500 MHz, D 2O, 25 C) of 1 3b.
11 fig. S5. 1D NOESY spectrum (500 MHz, D 2O, room temperature, irradiation at 7.96 ppm) of 1 3b. fig. S6. Concentration-dependent 1 H NMR spectra (500 MHz, D 2O, room temperature) of 13b. At (A) 0.8 mm and (B) 5.0 M, and (C) 1 at 0.8 mm.
12 fig. S7. ESI-TOF MS spectrum (H 2O, room temperature) of 1 3b at 5.0 μm. fig. S8. ESI-TOF MS spectrum (H 2O, room temperature) of 13b.
13 fig. S9. Optimized structure of 1 3b (R = -OCH3).
14 fig. S10. 1 H NMR spectra (500 MHz, D 2O, room temperature) of 12a. (A) Aromatic to aliphatic and (B) aliphatic regions.
15 fig. S11. 1 H NMR spectra (500 MHz, D 2O, 60ºC) of 12a. (A) Aromatic to aliphatic and (B) aliphatic regions.
16 A j' j k k' R R R h i b a g N Pt N f e OH d HO O c HO HO HO OHO O HO OH R R R 4+ j k l R = O OMe N Pt N 4NO 3 3 B A,H J E B,C F G K I D D I K G F B,C J E A,H OH F D E HO O C B A HO HO J HO OH O O I H K HO G OH fig. S12. 1 H- 1 H Correlation spectroscopy (COSY) spectra (500 MHz, D 2O, room temperature) of 12a. (A) Aromatic to aliphatic and (B) aliphatic regions.
17 A g i h f b' c' b d' c e' d e a D I K G F B,C J E k' R R R h i b a g N Pt N f e OH d D F E HO O C B c A HO J HO HO OHO O I K H HO G OH R R R 4+ A,H j k l R = O OMe N Pt N 4NO 3 3 B A,H J E B,C F G K I D D I K G F B,C J A,H E OH F D E HO O C B A HO HO J HO OH O O I H K HO G OH fig. S13. NOESY spectra (500 MHz, D 2O, room temperature) of 12a. (A) Aromatic and (B) aliphatic regions.
18 fig. S14. Homonuclear Hartmann-Hahn (HOHAHA) spectrum (500 MHz, D 2O, 60ºC) of 12a. fig. S15. Heteronuclear single quantum coherence (HSQC) NMR spectrum (500 MHz, D 2O, 60ºC) of 12a.
19 fig. S16. 1 H DOSY NMR spectrum (500 MHz, D 2O, room temperature) of 1 2a m/z [M 4NO 3 ] 4+ [M 3NO 3 ] 3+ [M 2NO 3 ] 2+ Found Found Found Calcd Calcd Calcd m/z fig. S17. ESI-TOF MS spectrum (H 2O, room temperature) of 12a.
20 fig. S18. 1 H NMR spectra (500 MHz, D 2O, room temperature) of 1 with various disaccharides. (A) Capsule 1 with (B) 2b, (C) 2c, (D) 2d, (E) 2e, or (F) 2f in D 2O. fig. S19. Optimized structure of 1 2a (R = -OCH 3).
21 fig. S20. A snapshot of 12a (R = -OCH 3) in water from molecular dynamics simulation. fig. S21. Temperature-dependent 1 H NMR spectra (500 MHz, D 2O) of 12a. (A) 25, (B) 35, (C) 45, (D) 55, (E) 65, and (F) 75ºC. Signals a HG and a H are derived from the inner protons of capsule 1 with and without guest 2a, respectively.
22 fig. S22. Concentration-dependent 1 H NMR spectra (500 MHz, D 2O, mm based on 1, room temperature) of 12a. (A) Capsule 1 and the mixtures of 1 and 2a with (B) 1.4, (C) 6.2, (D) 6.9, (E) 8.4, (F) 9.3, (G) 10.7, (H) 13.6, (I) 21.0, (J) 25.4, and (K) 43.0 equivalents. Signals a HG and a H are derived from the inner protons of capsule 1 with and without guest 2a, respectively. fig. S23. Selective encapsulation of 2a from a mixture of 2a and 2b by 1. 1 H NMR spectra (500 MHz, D 2O, room temperature) of (A) selective encapsulation of 2a from a mixture of 2a and 2b by 1 and (B) extracted 12a.
23 A free 2a & 2c encapsulated 2a B free 2a & 2d encapsulated 2a C free 2a & 2e encapsulated 2a D free 2a & 2f encapsulated 2a ppm fig. S24. Selective encapsulation of 2a from a mixture of 2a and various disaccharides by 1. 1 H NMR spectra (500 MHz, r.t.) of the selective encapsulation of 2a by 1 from a mixture of 2a and (A) 2c, (B) 2d, (C) 2e, or (D) 2f in D 2O.
24 fig. S25. Encapsulation of 4a within 1. (A) 1 H NMR (500 MHz, D 2O, room temperature) and (B) ESI-TOF MS (H 2O, room temperature) spectra of 14a.
25 fig. S26. Encapsulation of 4b within 1. 1 H NMR spectrum (500 MHz, D 2O, room temperature) of 14b. fig. S27. Concentration-dependent 1 H NMR spectra (500 MHz, D 2O, 0.8 mm based on 1, room temperature) of 14a and 14b. (A) Capsule 1, the mixtures of 1 and (B) 5.0 or (C) 1.0 eq. of 4a, the mixtures of 1 and (D) 5.0 or (E) 1.0 eq. of 4b.
26 fig. S28. Competitive binding experiments of 2a and artificial sugars by 1. 1 H NMR spectra (500 MHz, D 2O, room temperature) of selective encapsulation of (A) 4a and (B) 4b by 1 from a mixture of 2a and 4a,b. fig. S29. Competitive binding experiment of 4a and 4b by 1. 1 H NMR spectra (500 MHz, D 2O, room temperature) of (A) 14a and (B) 14b, and (C) after the competitive binding experiment of 4a and 4b by 1.
27 table S1. Theoretical binding energies of host-guest complexes (R = -OCH 3). E MM is the gas phase energy of a molecule, where intermolecular electrostatic and van der Waals energies as well as intramolecular interaction energy are taken into account. DG PB and DG SASA are the electrostatic contribution and the nonpolar contribution to the solvation free energy, rel rel rel respectively. DE MM, DDG solv, and DG bind are the relative gas phase energy difference, the relative solvation free energy change before and after the guest encapsulation, and the relative binding rel energy with respect to the D-sucrose s energies, e.g., DE MM (X) = DE MM (X) - DE MM (2a) for saccharide X. Assuming that all the host-guest complexes possess the same solvation free energies, the relative binding energy difference of saccharide X is defined as rel DG bind rel (X) = DE MM rel (X)+DDG solv (X).
28 table S2. Thermodynamic parameters of 1 2a. * [1 2a] and [1] were determined by 1 H NMR integral ratios of signals a HG and a H (fig. S18). [1] 0 = 0.35 mm, [2a] 0 = 3.9 mm. binding constant K = [1 2a]/([1] [2a]) M 1. table S3. Binding constants of 1 toward 2a in water.
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