Supramolecular Hydrogel Formation in a Series of Self-Assembling. Lipopeptides with Varying Lipid Chain Length.
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1 Supplementary Information Supramolecular Hydrogel Formation in a Series of Self-Assembling Lipopeptides with Varying Lipid Chain Length. V. Castelletto a, A. Kaur a, R. M. Kowalczyk a, I.W. Hamley a, M. Reza b, J. Ruokolainen b. a School of Chemistry, Pharmacy and Food Biosciences. University of Reading. Whiteknights, Reading RG6 6AD, United Kingdom. b Department of Applied Physics, Aalto University School of Science, Aalto FI-00076, Finland. 1
2 Table S1. Assignment of the peaks in the 1 H, 13 C NMR spectra. Atom 13 C chemical shift /ppm 1 H chemical shift/ ppm , , , Not resolved Not resolved , ,
3 , ?
4 Tables S2a, S2b and S2c: Parameters extracted from the SAXS fittings, displayed in Figures 6 and 12, to the data collected for solutions and hydrogels of 1, 2 and 3. Key: Gaussian bilayer form factor: scale factor N 1, Gaussian half-width at halfmaximum for polydispersity in layer thickness 2zH, inter-head group (layer) thickness 2z H, Gaussian half-width for outer layer surface σ H, electron density for headgroup ρ H, Gaussian half-width for inner layer σ C, relative electron density for inner layer ρ C, total bilayer thickness l T, calculated length of the extended molecule l. Caillé structure factor: diffuse scattering ν; total number of layers n 1 ; stacking separation d s ; stacking disorder parameter η. Cylinder form factor. scale factor N c, Gaussian half-width at half-maximum for polydispersity R c, cylinder radius R c, electron density ρ Cy, S2a Parameter 1 concentration 0.5 wt% (sol) 2 wt% (sol) 1 wt% (Hydrogel) N 1 [arb. units] x10-3 2zH [Å] z H [Å] σ H [Å] ρ H [rel. units] 1.52x10-3 8x10-5 1x10-4 σ C [Å] ρ C [rel. units] -8.2x x x10-5 l T ~ (2z H +2σ H ) ± 2zH 57± ± ±18.7 [l= 55.6 Å] n 1 3 d s [Å] 50.0 η 0.34 ν 14 N 1i [arb. units] 1 2zHi [Å] 2 2z Hi [Å] 22 σ Hi [Å] 10 ρ Hi [rel. units] 1.5x10-3 σ Ci [Å] 10 ρ Ci [rel. units] -3x10-5 4
5 l Ti ~ (2z Hi +2σ Hi ) ± 2zHi 32±2 n 1i 3 d si [Å] 22 ηi 0.1 νi 3 N c R c [Å] 20 R c [Å] 70 ρ cy [rel. units] 5x10-4 S2b Parameter 2 concentration 0.5 wt% (sol) 4 wt% (sol) 1 wt% (Hydrogel) N 1 [arb. units] x10-3 2zH [Å] z H [Å] σ H [Å] ρ H [rel. units] 3.7x x10-4 1x10-4 σ C [Å] ρ C [rel. units] -2.5x x x10-5 l T ~ (2z H +2σ H ) ± 2zH 53± ± ±18.7 [l= 57.6 Å] N d s [Å] 60.8 η 0.34 ν
6 S2c Parameter 3 concentration 0.5 wt% (sol) 2 wt% (sol) 1 wt% (Hydrogel) N 1 [arb. units] zH [Å] z H [Å] σ H [Å] ρ H [rel. units] 1.5x x x10-6 σ C [Å] ρ C [rel. units] -8.2x x x10-7 l T ~ (2z H +2σ H ) ± 2zH 56.9± ± ±16.9 [l= 59.6 Å] N d s [Å] 62 η 0.34 ν 19 6
7 Scheme S1. Chemical structure of lipopeptide 3. Numbers are used for the NMR spectra indexation in Table S1. 7
8 Figure S1. ES-MS spectra for lipopeptides (a) 1, (b) 2 and (b) 3. The expected molar masses are , g and g mol -1 for 1, 2 and 3 respectively 8
9 aggregation tendency of residue / % wt% YEALRVANEVTLN 20 o C, ph 7, Ionic strenght= 5x10-4 M Tendency to form: β-sheet, β-turn α-helix 0.15 wt% YEALRVANEVTLN 20 o C, ph 10, Ionic strenght= 2x10-3 M Tendency to form: β-sheet, β-turn α-helix (a) (b) 0 Y E A L R V A N E V T L N Aminoacids Figure S2. Prediction of the aggregation state for a given residue calculated using TANGO software for the peptide block in Lipopeptides 1, 2, and 3. 9
10 8 1, 2, 3 6 ph concentration / wt% Figure S3. ph as a function concentration for solutions of the three lipopeptides in water. 10
11 10-5 x[θ] / degrees cm 2 dmol (a) 3x10-2 wt% lipopetide 3: 5, 25 hrs after mixing in water 3x10-3 wt% lipopetide 3: 5, 25 hrs after mixing in water λ / nm 1.0 ( b ) Intensity / a. u hrs after mixing 3 in water. wt% lipopetide 3: 3x10-3, 3x R H / nm Figure S4. (a) CD signal measured for 3x10-3 and 3x10-2 wt% lipopetide 3 at 5 hrs and 25 hrs after mixing the lipopeptide in water. (b) Hydrodynamic radius R H measured at 25 hrs after mixing the lipopeptide 3 in water for 3x10-3 and 3x10-2 wt% lipopetide. 11
12 Figure S5. 2D XRD data. Top row: stalks prepared from 1 wt% solutions of lipopeptides (a) 1, (b) 2 and (c) 3. Bottom row: stalks prepared from hydrogels (1 wt%) of (d) 1, (e) 2 and (f) 3. 12
13 (a) (b) (c) (d) Figure S6. Comparison of the NMR spectra recorded at 700 MHz (blue) and 500 MHz (red), (a) 0 5 ppm region, (b) ppm, (c) 6 10 ppm and (d) ppm. The amplitude of both spectra were normalised to the amplitude of the DMSOd6 peak at 2.5 ppm. 13
14 Figure S7. ES-MSI spectra from an enzymatic assay of a solution containing 0.1 wt% 3 and 0.3 wt% asparaginase incubated at 37 o C with ph 8.6: (a) retention time curve and deconvolution of the retention time intensity (a) around 7.99 min and (c) within the range min. Mw values of 3 and asparaginase can be identified from MS-ESI spectra in (b) and (c) respectively, showing that the lipopeptide has not been degraded by the enzyme. 14
15 10-5 x[θ] / degrees cm 2 dmol 3 0 b a c 20 o C 6.5x10-3 wt% lipopetide 1 a- ph 6.14 b- ph 10 c- ph λ / nm Figure S8. CD data for a solution of 6.5 wt% lipopetide 1. The ph of an initial solution in water (ph 6.14) was raised to ph 10 and then decreases to ph The CD was measured for the different ph conditions. 15
16 G' lipopeptide: 1, 2 and 3 G" lipopeptide: 1, 2 and 3 G', G'' / Pa 1E+04 1E osc. stress / Pa Figure S9. Stress dependence of the shear moduli (at a frequency rad s -1 ) showing the linear regime for hydrogels prepared from 1 wt% lipopeptide 1, 2 or 3. 16
17 11.91Å 4.72 Å 4.7 Å 4.1 Å 3.68 Å 3.79 Å 3.25 Å 2.82 Å 2.39 Å 2.39 Å 10.5Å 3.8 Å 11.1 Å 5.49 Å 4.7 Å Intensity / a. u Å Å 2 1 wt % lipopeptide q / Å -1 3 Figure S10. XRD profiles for hydrogels prepared from 1 wt% lipopeptide (a) 1, (b) 2 and (c) 3. 17
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