Deciphering the Rules for Amino Acid Co- Assembly Based on Interlayer Distances
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1 Supporting Information Deciphering the Rules for Amino Acid Co- Assembly Based on Interlayer Distances Santu Bera, Sudipta Mondal, Yiming Tang, Guy Jacoby, Elad Arad, ǁ Tom Guterman, Raz Jelinek, ǁ Roy Beck, Guanghong Wei, and Ehud Gazit * Department of Molecular Microbiology and Biotechnology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Tel Aviv, 69978, Israel Department of Physics, State Key Laboratory of Surface Physics, Key Laboratory for Computational Physical Sciences (MOE), Fudan University, Shanghai, , People's Republic of China The Raymond and Beverly Sackler School of Physics and Astronomy, Tel Aviv University, Tel Aviv 69978, Israel ǁ Department of Chemistry, Ilse Katz Institute (IKI) for Nanoscale Science and Technology, Ben Gurion University of the Negev, Beer Sheva , Israel 1
2 Figure S1. Supramolecular β-sheet-like structure of amino acids. 29 Parallel and antiparallel β- sheet-like structure of Ile and Phe respectively. 2
3 Figure S2. Interlayer separation distances of a) Phe, b) Ile, c) Met, d) Gly and e) Ala. 29 Figure S3. High resolution scanning electron microscopic (HRSEM) images of a) Phe, b) Ile, c) Met alone, d) Phe:Ile (1:1) mixture, and e) Phe:Met (1:1) mixture. The co-assembly nature of Phe:Ile and Phe:Met was observed by simple mixing of two separately prepared amino acid solutions. 3
4 Figure S4. High resolution mass spectra obtained from ToF-SIMS experiments using samples prepared by vapor deposition of Phe and Ile mixture and a magnified image. Figure S5. ToF-SIMS ion image of the Phe:Ile conjugate, corresponding to mass
5 Figure S6. High resolution mass spectra obtained from ToF-SIMS experiments using samples prepared by vapor deposition of Phe and Met mixture. a) The lower region showed peaks at 150, corresponding to Met, and at 166, corresponding to Phe. b) Magnified image indicating the presence of a peak at 315, corresponding to the Phe:Met conjugate. 5
6 Figure S7. Coated surfaces after vapor deposition of Phe:Met. a) HRSEM image. b) ToF-SIMS ion images of (left to right) Phe labelled in red, Met labelled in green and overlap of Phe and Met with corresponding color. Figure S8. High resolution mass spectra obtained from ToF-SIMS experiments for the samples prepared by vapor deposition of Phe and Gly mixture. 6
7 Figure S9. Coated surfaces after vapor deposition: HRSEM image of Phe, Ala and Phe:Ala deposition. Figure S10. High resolution mass spectrum analysis obtained from ToF-SIMS experiments using samples prepared by vapor deposition of a Phe and Ala mixture, showing a peak only at 166, corresponding to Phe. 7
8 Figure S11. a) Raw data of the heat pattern during amino acids binding. Pink- Phe:Ile, cyan- Phe:Met, blue- Phe:Gly, olive- Phe:Ala and Gray- Phe:buffer. b) Curves showing the enthalpy changes with increasing the Phe molar fraction. Data were fitted using an independent binding model. 8
9 Figure S12. Schematic diagram and parameters of refined main-chain representations in coarsegrained model for amino acids. 9
10 Figure S13. High resolution scanning electron microscopy (HRSEM) images of a) Phe, b) Trp, c) Val, d) Leu, e) Pro, f) Thr, g) Asp alone, h) Phe:Trp (1:1) mixture, i) Phe:Val (1:1) mixture, j) Phe:Leu (1:1) mixture, k) mixed system of Phe and Pro (1:1) showing the presence of both Phe elongated fibers and small rod shape structures of Pro, l) mixed system of Phe and Thr (1:1) displaying only long fibers of Phe as Thr does not form any definite self-assembled structure, m) mixed system of Phe and Asp (1:1) containing both Phe fibers and Asp flake structures. Scale bars are indicated in each image. Table S1. Classification of amino acids based on interlayer separation distance in crystal structure. 29 Amino acid Interlayer distance (Å) β-sheet propensity L-Trp L-Phe F-I F-II F-III F-IV high L-Met L-Ile L-Leu L-Val L-Cys monoclinic orthorhombic L-Tyr
11 L-His monoclinic orthorhombic L-Ser moderate L-Glu α form β form L-Asn L-Gln L-Asp L-Thr L-Ala Gly α-form β-form Low L-Pro
12 Table S2. Thermodynamic properties of amino acids binding as determined by the ITC measurements. Amino acids Parameter Value Standard Deviation Combination Phe:Ile K d (M) 1.02x x10-5 ΔH (kj/mol) ΔS (J/mol K) Phe:Met K d (M) 1.85x x10-5 ΔH (kj/mol) ΔS (J/mol K) Phe:Gly K d (M) 6.77x x10-6 ΔH (kj/mol) ΔS (J/mol K) Phe:Ala K d (M) 7.08x x10-6 ΔH (kj/mol) ΔS (J/mol K) Table S3. Charges of N-terminal and C-terminal of phenylalanine, isoleucine and glycine based on quantum mechanical calculations. Phenylalanine Isoleucine Glycine N terminal C terminal N terminal C terminal N terminal C terminal Charge (e)
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