Supporting Information. Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on
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- Άτροπος Λειβαδάς
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1 Supporting Information for Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity Marta De Zotti 1, Barbara Biondi 1, Cristina Peggion 1, Matteo De Poli 1, Haleh Fathi 1, Simona Oancea 2, Claudio Toniolo 1 and Fernando Formaggio* 1 Address: 1 ICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Padova, Italy and 2 Department of Biochemistry and Toxicology, Lucian Blaga University of Sibiu, Sibiu, Romania Fernando Formaggio* - fernando.formaggio@unipd.it *Corresponding author Chemical characterization data for the peptides reported in Schemes 1 3. S1
![Table S-I: ROE constraints, deviations from idealized geometry, and mean energies for the NMR-based structures (energy < 144 kcal/mol) of ψ[cs-nh] 9.](/docs-images/55/36423635/images/2-0.png "Number of NOEs total 69 intraresidue 24 sequential 23 i,i+n, n = 2, 3, 4 22 Mean rmsd (a) from ideality of accepted structures bonds (Å) 0.0086 angles ( ) 1.05 impropers ( ) 67.0 ROEs (Å) 0.")
2 Table S-I: ROE constraints, deviations from idealized geometry, and mean energies for the NMR-based structures (energy < 144 kcal/mol) of ψ[cs-nh] 9. Number of NOEs total 69 intraresidue 24 sequential 23 i,i+n, n = 2, 3, 4 22 Mean rmsd (a) from ideality of accepted structures bonds (Å) angles ( ) 1.05 impropers ( ) 67.0 ROEs (Å) Mean energies (kcal/mol) of accepted structures E overall E bond 12.6 E angle 46.7 E ROE 44.3 (a) Root-mean-square deviation. Table S-II: Average values ( ) for the torsion angles m and m and their relative standard deviations resulting from the 18 calculated structures (energy < 144 kcal/mol) of ψ[cs-nh] 9 (400 MHz, 1 mm in CD 3 CN solution, 298 K). Residue m Δ m Δ Aib Gly L-Leu Aib Gly Gly L-Leu Aib Gly 9 (CS) L-Ile L-Leu-OMe Figure S-I: Representation of the 18 3D structures with energy < 144 kcal/mol resulting from the MD calculations of ψ[cs-nh] 9 with the backbone atoms of residues 4 11 superimposed. S2
3 Chemical characterization data for the peptides reported in Schemes 1 3 and not characterized elsewhere [1-5] Boc-Aib-Gly-Ile-Leu-OMe: mp C; R f1 0.40; R f2 0.85; R f3 0.30; [α] D : 91.1 (c 0.1, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 7.86 (d, 1H, Ile NH), 7.00 (t, 1H, Gly NH), 6.77 (d, 1H, Leu NH), 5.02 (s, 1H, Aib NH), (m, 1H, Leu α-ch), (m, 1H, Ile α- CH), (d, 2H, Gly α-ch 2 ), 3.70 (s, 3H, OMe CH 3 ), 2.07 (m, 1H, Ile β-ch), (m, H, Leu γ-ch, Boc 3 CH 3, Aib 2 β-ch 3, Leu β-ch 2, Ile γ-ch 2 ), (m, 12H, Leu 2 δ-ch 3, Ile γ- and δ-ch 3 ); IR (KBr) 3288, 1756, 1652, 1526 cm 1. Boc-Gly-Leu-Aib-Gly-Ile-Leu-OMe: mp C; R f1 0.40; R f2 0.95; R f3 0.30; 1 H NMR (0 MHz, CDCl 3 ) (d, 1H, Leu NH), (m, 2H, Ile NH, Gly NH), 6.99 (s, 1H, Aib NH), (d, 1H, Leu NH), (t, 1H, Gly NH), (m, 10H, 2 Leu α-ch, Ile α-ch, 2 Gly α-ch 2, OMe CH 3 ), 2.08 (m, 1H, Ile β-ch), (m, 14H, 2 Leu β-ch 2, 2 Leu γ-ch, Aib 2 β-ch 3 ), 1.41 (s, 9H, Boc 3 CH 3, Ile γ-ch 2 ), (m, 18H, 2 Leu 2 δ-ch 3, Ile γ- and δ-ch 3 ); IR (KBr): 3315, 1654, 1536 cm 1. Boc-Gly-ψ[CS-NH]-Leu-Aib-OMe: mp C; R f1 0.90; R f2 0.90; R f3 0.45; [α] D 58.8 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 8.97 (d, 1H, Leu NH), 7.08 (s,1h, Aib NH), 5.51 (m, 1H, Gly NH), 4.43 (m, 2H, Gly α-ch 2 ), 4.12 (m, 1H, Leu α-ch), 3.71 (s, 3H, OMe CH 3 ), 1.66 (m, 3H; Leu β-ch 2 and γ-ch), 1.51 (m, 6H, Aib 2 β-ch 3 ), 1.41 (s, 9H Boc 3 CH 3 ), 0.93 (d, 6H, Leu 2 δ-ch 3 ); IR (KBr): 3446, 3280, 1738, 17, 1694, 1652, 1547, 1526 cm 1. Boc-Aib-Gly-ψ[CS-NH]-Leu-Aib-OMe: mp C; R f1 0.85; R f2 0.90; R f3 0.; [α] D 40.9 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 8.97 (d, 1H, Leu NH) 7.08 (s,1h, Aib NH), 6.10 (s,1h, Aib NH), 5.51 (m, 1H, Gly NH), 4.43 (m, 2H, Gly α-ch 2 ), 4.12 (m, 1H, Leu α-ch), 3.71 (s, 3H, OMe CH 3 ), 1.66 (m, 3H; 2H Leu β-ch 2 and γ-ch), 1.51 (m, 12H, 2 Aib 2 β-ch 3 ), 1.41 (s, 9H Boc 3 CH 3 ), 0.93 (d, 6H, Leu 2 δ-ch 3 ); IR (KBr): 3349, 3265, 1717, 1691, 1665, 1510 cm 1. S3
4 n-oct-aib-gly-ψ[cs-nh]-leu-aib-ome: oil; R f1 0.81; R f2 0.90; R f3 0.15; [α] D 5.68 (c 0.2, MeOH); 1 H NMR (0 MHz, CDCl3) δ 8.97 (d, 1H, Leu NH) 7.08 (s, 1H, Aib NH), 6.10 (s, 1H, Aib NH), 5.51 (m, 1H, Gly NH), 4.43 (m, 2H, Gly α-ch 2 ), 4.12 (m, 1H, Leu α-ch), 3.71 (s, 3H, OMe CH 3 ), 2.28 (m, 2H, n-oct β-ch 2 ), 1.66 (m, 3H, Leu β-ch 2 and γ-ch), 1.51 (m, 12H, 2 Aib 2 β-ch 3 ), 1.26 (m, 10H, n-oct 5 CH 2 ), (m, 9H, Leu 2 δ-ch 3 and n- Oct ω-ch 3 ); IR (KBr): 3313, 3240, 1742, 1730, 1650, 1531 cm 1. n-oct-aib-gly-ψ[cs-nh]-leu-aib-oh: R f1 0.10; R f2 0.70; R f3 0.00; 1 H NMR (0 MHz, CDCl 3 ) δ 8.97 (d, 1H, Leu NH) 7.08 (s, 1H, Aib NH), 6.10 (s, 1H, Aib NH), 5.51 (m, 1H, Gly NH), 4.43 (m, 2H, Gly α-ch 2 ), 4.12 (m, 1H, Leu α-ch), 2.28 (m, 2H, n-oct β-ch 2 ), 1.66 (m, 3H, Leu β-ch 2 and γ-ch), 1.51 (m, 12H, 2 Aib 2 β-ch 3 ), 1.26 (m, 10H, n-oct 5 CH 2 ), (m, 9H, Leu 2 δ-ch 3 and n-oct ω-ch 3 ); IR (KBr): 3310, 3044,17, 1650, 1531 cm 1. n-oct-aib-gly-ψ[cs-nh]-leu-aib-gly-gly-leu-aib-gly-ile-leu-ome: mp C; R f1 0.; R f2 0.85; R f3 0.00; [α] D (c 0.5, MeOH); 1 H NMR (400 MHz, CD 3 CN) 9.30 (d, 1H, NH Leu 3 ), 7.77 (t, 1H, NH Gly 6 ), 7.49 (t, 1H, NH Gly 2 ), 7.47 (t, 1H, NH Gly 5 ), 7.47 (s, 1H, NH Aib 4 ), 7.42 (t, 1H, NH Gly 9 ), 7.40 (d, 1H, NH Leu 7 ), 7.37 (s, 1H, NH Aib 8 ), 7.30 (d, 1H, NH Ile 10 ), 7.22 (s, 1H, NH Aib 1 ), 7.12 (d, 1H, NH Leu 11 ), 4.21 (m, 1H, α-ch Leu 11 ), 4. (m, 1H, α-ch Leu 7 ), 4.17 (m, 1H, α-ch Leu 3 ), 4.05 (dd, 1H, α-ch Ile 10 ), 3.78 (dd, 1H, 1 α-ch Gly 6 ), 3.74 (dd, 1H, 1 α-ch Gly 6 ), 3.71 (s, 3H, CH 3 OMe), 3.67 (dd, 1H, 1 α-ch Gly 9 ), 3.65 (dd, 1H, 1 α-ch Gly 2 ), 3.64 (m, 2H, α-ch 2 Gly 5 ), 3.60 (dd, 1H, 1 α-ch Gly 9 ), 3.58 (dd, 1H, 1 α-ch Gly 2 ), 2.15 (t, 2H, β-ch 2 n-oct), 1.50 (m, 2H, γ-ch 2 n-oct), 2.15 (m, 2H, δ-ch 2 n-oct), 1.84 (m, 1H, β-ch Ile 10 ), 1.53 (m, 2H, β-ch 2 Leu 7 ), 1.53 (m, 2H, β-ch 2 Leu 3 ), 1.62 (m, 1H, γ-ch Leu 3 ), 1.60 (m, 1H, γ-ch Leu 7 ), 1.59 (m, 1H, γ-ch Leu 11 ), 1.48 (m, 1H, 1 β- CH Leu 11 ), 1.53 (m, 1H, 1 β-ch Leu 11 ), 1.45 (m, 1H, γ-ch Ile 10 ), 1.36 (s, 6H, 2 β-ch 3 Aib 4 ), 1.35 (s, 6H, 2 β-ch 3 Aib 8 ), 1.32 (s, 6H, 2 β-ch 3 Aib 1 ), 1.17 (m, 1H, 1 γ-ch Ile 10 ), 0.88 (m, 3H, δ-ch 3 Leu 3 ), 0.87 (m, 3H, δ-ch 3 Leu 11 ), 0.86 (d, 3H, γ-ch 3 Ile 10 ), 0.83 (m, 3H, δ-ch 3 Leu 3 ), 0.81 (m, 3H, δ-ch 3 Ile 10 ), 0.80 (t, 3H, ω-ch 3 n-oct), 0.78 (m, 3H, δ-ch 3 Leu 11 ); IR (KBr): 3314, 3057, 1744, 1656, 1537 cm 1. Z-Gly-Leu-Aib-Ot-Bu: mp C; R f1 0.80; R f2 0.65; R f3 0.50; [α] D 39.0 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 7.33 (m, 5H, Z Ph), 6.85 (s, 1H, Aib NH), 6.79 (d, S4
5 1H, Leu NH), 5.70 (t, 1H, Gly NH), 5.10 (s, 2H, Z CH 2 ), 4.40 (m, 1H, Leu α-ch), 3.86 (t, 2H, Gly α-ch 2 ), 1.58 (m, 3H; Leu β-ch 2 and γ-ch), 1.51 (2s, 6H, Aib 2 β-ch 3 ), 1.43 (s, 9H, Ot- Bu 3 CH 3 ), 0.91 (d, 6H, Leu 2 δ-ch 3 ); IR (KBr): 3324, 1731, 1705, 1659, 1546 cm 1. Z-Aib-Gly-Leu-Aib-Ot-Bu: mp C; R f1 0.50; R f2 0.80; R f3 0.30; [α] D 3.2 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 7.36 (m, 6H, Z Ph and 1 NH), 6.93 (m, 1H, NH), 6.87 (s, 1H, Aib NH), 5.37 (s, 1H, Aib NH), 5.10 (2d, 2H, Z CH 2 ), 4.42 (m, 1H, Leu α-ch), 3.93 (d, 2H, Gly α-ch 2 ), (m, 3H, Leu β-ch 2 and γ-ch), (m, 12H, 2 Aib 2 β- CH 3 ), 1.42 (s, 9H, Ot-Bu 3 CH 3 ), 0.91 (m, 6H, 2 Leu δ-ch 3 ); IR (KBr): 3316, 1732, 1701, 1659, 1536 cm 1. n-oct-aib-gly-leu-aib-ot-bu: mp C; R f1 0.45; R f2 0.55; R f3 0.30; [α] D 2.58 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 6.93 (m, 1H, NH), 6.87 (s, 1H, Aib NH), 5.37 (s, 1H, Aib NH), 4.42 (m, 1H, Leu α-ch), 3.93 (d, 2H, Gly α-ch 2 ), 2.23 (m, 2H n-oct β-ch 2 ) (m, 3H, Leu β-ch 2 and γ-ch), (m, 12H, 2 Aib 2 β-ch 3 ), 1.42 (s, 9H, Ot-Bu 3 CH 3 ), 1.26 (m, 10H, n-oct 5 CH 2 ), (m, 6H, 2 Leu δ-ch 3, n-oct ω-ch 3 ); IR (KBr): 3315, 1740, 1709, 1656, 1536 cm 1. Fmoc-Gly-ψ[CS-NH]-Gly-Leu-Aib-Ot-Bu: mp C; R f1 0.72; R f2 0.94; R f3 0.22; [α] D 18.6 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 8,98 (t, 1H, Gly NH), 7.75 (d, 2H, Fmoc), 7.58 (t, 2H, Fmoc), 7.49 (m, 2H, Fmoc), 6.81 (s, 1H, Aib NH), 6.67 (t, 1H, Leu NH), 5.99 (t, 1H, Gly NH), 5.02 (m, H, Leu α-ch), (m,3H, Fmoc), (d, 4H, 2Gly α-ch 2 ), (m, 9H, Leu β-ch 2 and γ-ch, Aib 2 β-ch 3 ), 1.43 (s, 9H, Ot-Bu 3 CH 3 ), 0.92 (m, 6H, Leu 2 δ-ch 3 ); IR (KBr): 3299, 1730, 1706, 1658, 1528 cm 1. Fmoc-Gly-ψ[CS-NH]-Gly-Leu-Aib-Gly-Ile-Leu-OMe: mp C; R f1 0.74; R f2 0.92; R f3 0.15; [α] D 17.3 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) δ 8.98 (t, 1H, Gly NH), 7.86 (d, 1H, Ile NH), 7.75 (d, 2H, Fmoc), 7.58 (t, 2H, Fmoc), 7.49 (m, 2H, Fmoc), 7.00 (t, 1H, Gly NH), 6.81 (s, 1H, Aib NH), 6.67 (m, 2H, 2 Leu NH), 5.99 (t, 1H, Gly NH), 5.02 (m, 2H, 2 Leu α-ch), (m, 3H, Fmoc), (m, 1H, Ile α-ch), (d, 6H, 3Gly α-ch 2 ), 2.07 (m, 1H, Ile β-ch), (m, 14H, 2 Leu β-ch 2 and γ-ch, Aib 2 -CH 3, Ile γ-ch 2 ), 1.43 (s, 9H, Ot-Bu 3 CH 3 ), (m, 24H, 2 Leu 2 -CH 3, Ile γ-ch 3 and δ-ch 3 ); IR (KBr): 3309, 3065, 1730, 1656, 1531cm 1. S5
6 n-oct-aib-gly-leu-aib-gly-ψ[cs-nh]-gly-leu-aib-gly-ile-leu-ome: mp C; R f1 0.; R f2 0.85; R f3 0.00; [α] D 21.3 (c 0.5, MeOH); 1 H NMR (0 MHz, CD 3 CN) 9.42 (t, 1H, NH Gly 6 ), 7.75 (t, 1H, NH Gly 5 ), 7.67 (d, 1H, NH Leu 3 ), (s, 1H, NH Aib 4 ), 7.40 (t, 1H, NH Gly 2 ), 7.33 (t, 1H, NH Gly 9 ), 7.29 (d, 1H, NH Ile 10 ), 7.28 (d, 1H, NH Leu 7 ), 7.27 (s, 1H, NH Aib 8 ), 7.17 (s, 1H, NH Aib 1 ), 7.07 (d, 1H, NH Leu 11 ), 4.21 (m, 1H, α-ch Leu 11 ), 4. (m, 1H, α-ch Leu 7 ), 4.17 (m, 1H, α-ch Leu 3 ), 4.05 (dd, 1H, α-ch Ile 10 ), 3.78 (dd, 1H, 1 α-ch Gly 6 ), 3.74 (dd, 1H, 1 α-ch Gly 6 ), 3.71 (s, 3H, CH 3 OMe), 3.67 (dd, 1H, 1 α-ch Gly 9 ), 3.65 (dd, 1H, 1 α-ch Gly 2 ), 3.64 (m, 2H, α-ch Gly 5 ), 3.60 (dd, 1H, 1 α-ch Gly 9 ), 3.58 (dd, 1H, 1 α-ch Gly 2 ), 2.15 (t, 2H, β-ch 2 n-oct), 2.15 (m, 2H, δ-ch 2 n-oct), 1.84 (m, 1H, β-ch Ile 10 ), 1.68 (m, 1H, γ-ch Leu 3 ), 1.60 (m, 1H, γ-ch Leu 7 ), 1.59 (m, 1H, γ-ch Leu 11 ), 1.53 (m, 1H, 1 β-ch Leu 11 ), 1.53 (m, 2H, β-ch 2 Leu 7 ), 1.53 (m, 2H, β-ch 2 Leu 3 ), 1.50 (m, 2H, γ-ch 2 n-oct), 1.48 (m, 1H, 1 β-ch Leu 11 ), 1.47 (m, 1H, γ-ch 2 Ile 10 ), 1.46 (s, 6H, 2 β-ch 3 Aib 4 ), 1.35 (s, 6H, 2 β-ch 3 Aib 8 ), 1.32 (s, 6H, 2 β-ch 3 Aib 1 ), 1.28 (m, 1H, 1 γ-ch 2 Ile 10 ), 0.88 (m, 3H, δ-ch 3 Leu 3 ), 0.87 (m, 3H, δ-ch 3 Leu 11 ), 0.86 (d, 3H, γ-ch 3 Ile 10 ), 0.83 (m, 3H, δ-ch 3 Leu 3 ), 0.81 (m, 3H, δ-ch 3 Ile 10 ), 0.80 (t, 3H, ω-ch 3 n-oct), 0.78 (m, 3H, δ-ch 3 Leu 11 ); IR (KBr): 3302, 1742, 1657, 1651, 1536 cm 1. Boc-Gly-ψ[CS-NH]-Ile-Leu-OMe: oil; R f1 0.90; R f2 0.92; R f3 0.60; [α] D 56.1 (c 0.5, MeOH); 1 H NMR (0 MHz, CDCl 3 ) 8.74 (d, 1H, Ile NH), (d, 1H, Leu NH), (t, 1H, Gly NH), (m, 4H, Ile αch, Leu αch, Gly αch 2 ), 3.71 (s, 3H, OMe CH 3 ), (m, 6H, Ile -CH and -CH 2, Leu -CH 2 and -CH), 1.44 (s, 9H, Boc 3 CH 3 ), (m, 12H, Leu 2 -CH 3, Ile -CH 3 and -CH 3 ); IR (KBr): 3313, 1747, 1721, 1659, 1594, 1524 cm 1. n-oct-aib-gly-leu-aib-gly-gly-leu-aib-gly-ψ[cs-nh]-ile-leu-ome: oil; R f1 0.; R f2 0.87; R f3 0.00; [α] D 23.3 (c 0.2, MeOH); 1 H NMR (400 MHz, CD 3 CN) 8.96 (d, 1H, NH Ile 10 ), 7.91(t, 1H, NH Gly 6 ), 7.84 (t, 1H, NH Gly 5 ), 7.74 (d, 1H, NH Leu 3 ), 7.69 (t, 1H, NH Gly 2 ), 7.66 (t, 1H, NH Gly 9 ), 7.60 (d, 1H, NH Leu 7 ), (s, 1H, NH Aib 4 ), 7.52 (s, 1H, NH Aib 8 ), 7.35 (s, 1H, NH Aib 1 ), 7.13 (d, 1H, NH Leu 11 ), 4.21 (m, 1H, α-ch Leu 11 ), 4. (m, 1H, α-ch Leu 7 ), 4.17 (m, 1H, α-ch Leu 3 ), 4.05 (dd, 1H, α-ch Ile 10 ), 3.78 (dd, 1H, 1 α-ch Gly 6 ), 3.74 (dd, 1H, 1 α-ch Gly 6 ), 3.71(s, 3H, CH 3 OMe), 3.68 (dd, 1H, 1 α-ch Gly 9 ), 3.66 (dd, 1H, S6
7 1 α-ch Gly 2 ), 3.64 (m, 2H, α-ch 2 Gly 5 ), 3.60 (dd, 1H, 1 α-ch Gly 9 ), 3.58 (dd, 1H, 1 α-ch Gly 2 ), 2.25 (t, 2H, β-ch 2 n-oct), 1.57 (m, 2H, γ-ch 2 n-oct), 2.15 (m, 2H, δ-ch 2 n-oct), 1.84 (m, 1H, β-ch Ile 10 ), 1.53 (m, 2H, β-ch 2 Leu 7 ), 1.53 (m, 2H, β-ch 2 Leu 3 ), 1.68 (m, 1H, γ-ch Leu 3 ), 1.60 (m, 1H, γ-ch Leu 7 ), 1.59 (m, 1H, γ-ch Leu 11 ), 1.48 (m, 1H, 1 β-ch Leu 11 ), 1.53 (m, 1H, 1 β-ch Leu 11 ), 1.47 (m, 1H, γ-ch Ile 10 ), 1.46 (s, 6H, 2 β-ch 3 Aib 4 ), 1.35 (s, 6H, 2 β- CH 3 Aib 8 ), 1.32 (s, 6H, 2 β-ch 3 Aib 1 ), 1.28 (m, 1H, 1 γ-ch Ile 10 ), 0.88 (m, 3H, δ-ch 3 Leu 3 ), 0.86 (m, 3H, δ-ch 3 Leu 11 ), 0.84 (d, 3H, γ-ch 3 Ile 10 ), 0.83 (m, 3H, δ-ch 3 Leu 3 ), 0.82 (m, 3H, δ-ch 3 Ile 10 ), 0.79 (t, 3H, ω-ch 3 n-oct), 0.78 (m, 3H, δ-ch 3 Leu 11 ); IR (KBr): 3299, 1741, 1660, 1537 cm 1. References 1. De Zotti, M.; Biondi, B.; Peggion, C.; Formaggio, F.; Park, Y.; Hahm, K.-S.; Toniolo, C. Org. Biomol. Chem. 12, 10, doi: /c1ob06178j 2. Gurunath, R.; Balaram, P. Biopolymers 1995, 35, doi: /bip Iida, A.; Yoshimatsu, S.; Sanekata, M.; Fujita, T. Chem. Pharm. Bull. 1990, 38, doi: /cpb Brückner, H.; Koza, A. Amino Acids 03, 24, doi: /s x 5. Nagaraj, R.; Balaram, P. Tetrahedron 1981, 37, doi: /s (01)961-7 S7
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