Channels and Monomolecular Nanotubes

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1 Supporting nformation Control of Helix Formation by (E)- and (Z)-Double Bonds in Vinylogous γ-peptides A Way to on Channels and Monomolecular Nanotubes Carsten Baldauf, Robert Günther and Hans-Jörg Hofmann* nstitute of Biochemistry, Faculty of Biosciences, Pharmacy and Psychology, University of Leipzig, Brüderstraße 34, D Leipzig, Germany hofmann@uni-leipzig.de Contents Table S1: DFT/B3LYP/6-31G* Backbone Torsion Angles of the Conformers of 1 (n=1) S1 Table S2: PCM/HF/6-31G* Backbone Torsion Angles of the Conformers of 1 (n=1) S2 Table S3: DFT/B3LYP/6-31G* Backbone Torsion Angles of the Conformers of 1 (n=6, derived from the monomers) S3 Table S4: DFT/B3LYP/6-31G* Backbone Torsion Angles of the Conformers of 1 (n=6, obtained in the oligomer approach) S4 Table S5: Relative Enthalpies, Free Enthalpies and Entropies of the Conformers of 1 (n=6) S5 Table S6: DFT/B3LYP/6-31G* Backbone Torsion Angles of the Conformers of 2 (n=1) S6 Table S7: PCM/HF/6-31G* Backbone Torsion Angles of the Conformers of 2 (n=1) S7 Table S8: DFT/B3LYP/6-31G* Backbone Torsion Angles of the Conformers of 2 (n=6) S8 Table S9: Relative Enthalpies, Free Enthalpies and Entropies of the Conformers of 2 (n=6) S9 Table S10: HF/6-31G* Backbone Torsion Angles of the Conformers of 1 (n=11) S10 Coordinate files in the pdb -format are given for all hexamer structures and the undecamers H 22 and H 27.

2 Table S1. DFT/B3LYP/6-31G* Backbone Torsion Angles a for the Unsubstituted (U) and γ-methyl-substituted (G) Blocked Conformers of 1 (n=1) Conf. ϕ θ ζ ψ Conf. ϕ θ ζ ψ U G3a G3b U2a U2b G4a U2c G4b G4b' G1c b U3a G4c U3b G4c' G1b b U3c G5a G2a b U4a G5b U4b G6a G1a G6b G1b G1c G7a G7b G2a G7b' G2a' G7c G2b G2b' G2c G2c' a Torsion angles in degrees. b Optimization leads to the conformer after the arrow. S1

3 Table S2. PCM/HF/6-31G* Backbone Torsion Angles a for the Unsubstituted (U) and γ- Methyl- Substituted (G) Blocked Conformers of 1 (n=1) Conf. ϕ θ ζ ψ Conf. ϕ θ ζ ψ U G3a G3b U2a U2b G4a U2c G4b G4b' G1c b U3a G4c U3b G4c' G1b b U3c G5a U4a G5b G2c b U4b G6a G3a b G1a G6b G1b G1c G7a G7b G2a G7b' G2a' G7c G2b G2b' G2c G2c' a Torsion angles in degrees. b Optimization leads to the conformer after the arrow. S2

4 Table S3. DFT/B3LYP/6-31G* Backbone Torsion Angles a of all Periodic Hexamer Structures 1 (n=6) Derived from the Monomer Conformers U in Table 1 Conf. ϕ θ ζ ψ Conf. b ϕ θ ζ ψ (U1) (U3b) (U2a) (U3c) (U2b) (U4a) (U2c) 6 (H 27 ) (U4b) (U3a) a Angles in degrees. S3

5 Table S4. DFT/B3LYP/6-31G* Backbone Torsion Angles a for the Hydrogen-Bonded Helical Structures of the Hexamer 1 (n=6) Found in the Oligomer Approach Conf. b ϕ θ ζ ψ Conf. b ϕ θ ζ ψ H H H H H H H H a Angles in degrees. b H x denotes a helix with x-membered hydrogen-bonded pseudocycles. S4

6 Table S5. Relative Enthalpies, Free Enthalpies, Entropies, and Total Energies a at the HF/6-31G* level of ab initio MO theory of the Conformers of 1 (n=6) Conf. b H G S E T (U1) (U2a) (U2b) (U3a) (U3b) (U3c) (U4a) (U4b) H H H H 22 H H H H 27 /(U2c) a Relative enthalpies and relative free enthalpies in kj/mol; relative entropies in J/mol K; total energies in a.u. b H x denotes a helix with x-membered hydrogen-bonded pseudocycles. S5

7 Table S6. DFT/B3LYP/6-31G* Backbone Torsion Angles a for the Unsubstituted and γ- Methyl-Substituted (G) Blocked Conformers of 2 (n=1) Conf. ϕ θ ζ ψ Type b Conf. ϕ θ ζ ψ Type b U C 7 G U C 9 G U G6 G2 c U C 7 * G U G U G ax 63.1 C 9 U G C 7 * G G eq C 9 G C 7 * G ax C 7 G C 7 * G eq C 7 a Torsion angles in degrees. b C x denotes a hydrogen-bonded pseudocycle with x atoms, eq, ax: pseudoequatorial or pseudoaxial orientation of the C(γ) substituents. An asterisk denotes NH N hydrogen bonding. c Optimization leads to the conformer after the arrow. S6

8 Table S7. PCM/HF/6-31G* Backbone Torsion Angles a for the Unsubstituted and γ- Methyl-Substituted (G) Blocked Conformers of 2 (n=1) Conf. ϕ θ ζ ψ Type b Conf. ϕ θ ζ ψ Type b U C 7 G U C 9 G U G6 G4 c U C 7 * G U G U G ax 63.0 C 9 U G C 7 * G G eq C 9 G C 7 * G ax C 7 G C 7 * G eq C 7 a Torsion angles in degrees. b C x denotes a hydrogen-bonded pseudocycle with x atoms, eq, ax: pseudoequatorial or pseudoaxial orientation of the C(γ) substituents. An asterisk denotes NH N hydrogen bonding. c Optimization leads to the conformer after the arrow. S7

9 Table S8. DFT/B3LYP/6-31G* Backbone Torsion Angles a of all Periodic Hexamer Structures either Derived from the Monomers U in Table 6 or Obtained in the Oligomer Approach on Hexamers of 2 (n=6) Conf. b ϕ θ ζ ψ Conf. b ϕ θ ζ ψ H 7 (U1) H H 9 (U2) H H (U3) a Angles in degrees. b H x denotes a helix with hydrogen-bonded pseudocycles with x members. S8

10 Table S9. Relative Enthalpies, Free Enthalpies, Entropies, and Total Energies a at the HF/6-31G* level of ab initio MO theory of the Conformers of 2 (n=6) Conf. b H G S E T H 7 (U1) H 9 (U2) H H H (U3) a Relative enthalpies and relative free enthalpies in kj/mol; relative entropies in J/mol K; total energies in a.u. b H x denotes a helix with x-membered hydrogen-bonded pseudocycles. S9

11 Table S10. HF/6-31G* Backbone Torsion Angles a of Selected Undecamer Structures 1 (n=11) Conf. b ϕ θ ζ ψ H H H a Angles in degrees. b H x denotes a helix with x-membered hydrogen-bonded pseudocycles; total energies: H 19 : E T = a.u. H 22 : E T = a.u. H 27 : E T = a.u. S10

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