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1 riginaldokument gespeichert auf dem Dokumentenserver der Universität Basel edoc.unibas.ch Dieses Werk ist unter dem Vertrag Creative Commons amensnennung-keine kommerzielle utzung-keine Bearbeitung 3.0 Schweiz (CC BY-C-D 3.0 CH) lizenziert. Die vollständige Lizenz kann unter creativecommons.org/licenses/by-nc-nd/3.0/ch/ eingesehen werden
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17 π
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23 δ α C C ω C α 1 cis δ α C C ω C α 1 trans H C α ω C α 1 cis H C α ω C α 1 trans
24 π π
25 π π π π β π = = H Me
26 H Me H 3 C Ktrans/cis in D > 98% trans Me H 3 C H 3 C H Me CH 3 HMe
27 Me 3 (S) Me 3 (R) 2 5S 5R 6S 6R Me F (S) Me F (R) Me γ Ktrans/cis in D Hγ 3 H β' H δ' H H β δ C 2 CH 3 Ac H α C β 3 H δ H δ' Hγ Hγ' H β' H δ' H β H δ 3 C 2 CH 3 Ac H α C β H δ' 3 Hγ' H δ φφφ
28 σσ σσ Hδ 3 H δ' Cβ Hγ Cβ σ C- 3 H δ' Hγ H δ σ C-H anti gauche σ σ π γ
29 π
30 ω ω α φψω φψω
31
32 γ
33 CH 3 Ph C 2 CH 3 Ph C 2 CH 3 H H 2 a) 3 H C 2 CH 3 CuS 4 5H 2 a ascorbate H 2 : t-buh 8:1 RT, overnight C 2 CH 3 H 6 6 b) 3 3 H 3 Pd/C, HCl (aq), H 2 (g), MeH RT, 20 h Cl Cl H 3 H 3 H 3
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39 γ
40 H 2 H H 2 H 3 H 2 H H 2 H 2 H H 2 H 2 H H 2 CF H H H H H H H H H H H H 2 H H 2 H H 3 H 2 H 2 H 2 H 2 H 2
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42 β β H 2 H 3 H 2 H β Fl H H 2 7 Fl H H 2 7
43 R H H S H H S H H S H CF 4 PF 6 2 H 2 H H H H H B Fl H H H 8 H 2 H 2 H H B H H 2 H 2 H H 2 H 2 H H 2 H 2 H H 2 H
44 H H R 1 H R 2 a) proline-derived peptides R 3 H 2 * H H H cis-γ-amino-l-proline H H imidazolidine-2-carboxylic acid H * H H hydroxy proline R 2 R 3 R 1 b) amphiphatic oligoproline helices containing modified side chains H H L-proline c) (PPR) n, (PRR) n miniature proteins e) (VXLPPP) n = SAP amphiphatic proline-rich peptides d) (PX) n, proline-rich peptides derived from the antimicrobial peptide bactenicin 7 f) proline-based dendrimers γ
45 γ CF H H H H H H H 2 3 γ
46 H 3 H 2 H H 2 CF H H 2 CF H H 2 n = 2, 3 n = 2, 3 H 3 H H 2 H 2
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50 hydrophobic hydrophilic a) b)
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53 β
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55 δ ε ε
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57 a) H 2 H 2 H 2 H 2 H 3 H 3 H H CF H 3 H 2 CF H 3 H 2 b) H 2 H 2 H 2 H 2 H H CF H H 2 CF H H c) H 2 H H 2 CF H H 2 6
58 3 * Me BocH * Me X H 3 * Me BocH Boc H * Me H 2 X H 2 H * Me 7 8 X = CF 3 C 2 9 X = Cl X = CF 3 C 2 12 X = Cl 13 H 3 H 3 H 3 H 3 H H 3 3
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61 a) b) H 2 H 2 H 2 H H H 2 H 2 H H 2 HC H 3 H 2 HC H H 2 n = 3 m = 6 H H
62 a) b) H 2 H 2 H 2 H 2 H 3 H 3 H H CF H H 2 n = 2,3,4 CF H H 2 n = 2,3,4
63 a) b) H 2 H 2 H 2 H 2 H 2 H 2 H 2 H 2 H H H H CF H H 2 CF H H 2 n = 2,3,4 n = 2,3,4 c) H 2 H 2 d) H H 2 H H 2 CF H H 2 CF H H 2 n = 6,8 m = 3,4 6 3 e) H 2 H 2 f) H H 2 H H 2 CF H H 2 CF H H 2 n = 3,4 m = 6,8 3 6 a) b) H 2 H 2 H CF H H 2 * = R or S n = 6,8,10,12
64 a) H 2 H 2 H 2 H 2 H H * * CF H * = R or S 3 H 2 b) c) H 2 H 2 H * H 2 H * H 2 CF H H 2 CF H H 2 * = R or S 6 3 * = R or S 3 6
65 γ H H $$39 7 H H2 H FmocH H Strategy A H Staudinger reduction, cleavage from solid support CF 3 * Fmoc H 16 G SPPS, 5(6)-carboxyfluorescein labeling (3)n Strategy B Staudinger reduction BocH Boc H * C 2 H Fmoc 17 Strategy C H2 H FmocH H H SPPS, 5(6)-carboxyfluorescein labeling CF 3 C 2 H 3 n (H2)n CF G CPP CH2 CF G CF G BocH H Boc n Et3, Tf BocH HBoc Et3, Tf BocH HBoc BocH H Boc n BocH H Boc n CF G CH2 CF G Boc deprotection cleavage from solid support Boc deprotection & cleavage from solid support CF G CF 3 C 2 H 2 H 2 H n CPP CH2 ligoproline-based Cell Penetrating Peptides
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67 H2 SPPS Fmoc G (3)n a), b) CF G (3)n CH2 CF 3 C 2 BocH H 2 CF 3 C 2 Boc H 2 H 3 n H n H n c) d) e) CF G CPP CH2 CF G CH2 CF G CPP CH2
68 H2 SPPS Fmoc G (3)n a) CF G (3)n CF 3 C 2 BocH H 2 Boc H 2 (H2)n H n H n b) c) d) CF G CF G CF G CPP CH2
69 SPPS BocH H Boc n H2 Fmoc G CF 3 C 2 a) CF G BocH H Boc n b) CF G H 2 H CPP H 2 n CH2
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74 γ H HBoc BocH Boc H Pbf H H 3 H C 2 Me H C 2 Me H C 2 Me H 2 C 2 Me H C 2 Me pkb (calculated*) pkb (determined**) pkb ucleophilicity
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76 H H H Boc 2 (1.2 eq.), SCl 2 (1.5 eq.), MeH ahc 3 (2.3 eq.), dioxane/h 2 reflux, 19 h; quant. rt, 19 h; 77% H H H 2 Me Boc Cl Me a) Et 3 (1.2 eq.), MsCl (1.2 eq.), DCM, 0 C to rt, 2 h b) a 3 (5.0 eq.), DMF, 80 C, 17 h; 95% 3 Boc 56S Me ah (2.0 eq.), THF/H 2 /MeH rt, 3.5 h, 86% 3 Boc 57S H HCl/dioxane (4 M) rt, 5 h; 90% 3 Cl H 2 58S H FmocCl (1.2 eq.), ahc 3 (2.5 eq.), dioxane/h 2, rt, 3 h; quant. Fmoc H 3 16S
77 H Boc Me a) Methanesulfonic acid (1.2 eq.), Et 3 (0.4 eq.), PPh 3 (1.8 eq.), DIAD (1.9 eq.), toluene, 0 C - 70 C, 3.0 h b) a 3 (5.0 eq), DMF, 80 C, overnight; 95% 3 Boc Me ah (2.0 eq.), THF/H 2 /MeH, rt, 4.0 h; 95% 55 56R 57R 3 Boc H HCl/dioxane (4 M) rt, 2 h; quant. 3 Cl H 2 58R H Fmoc-Cl (1.2 eq.), ahc 3 (2.7 eq.), dioxane/h 2, rt, 6.5 h; 80% 3 Fmoc H 16R
78 H ah (2.0 eq), H H BnBr (1.1 eq), CbzCl (1.0 eq), H 2 Et 3 (1.1 eq), THF C 2 H C 2 H 0 C to rt, 2 d; H 0 C to rt, 5.5 h; 94% Cbz 68% Cbz C 2 Bn MsCl (1.2 eq), Et 3 (1.2 eq), DCM 0 C to rt, 2 h PPh 3 (2.0 eq), H 2 (2.0 eq), THF reflux, 5.5 h; quant. Ms H 2 a 3 (5.0 eq), DMF C 2 Bn 80 C, 22 h; C 2 Bn Cbz 92 % Cbz BocH Tf H BocH HBoc (1.0 eq) 18 C 2 Bn Et 3 (1.0 eq), DCM, Cbz 0 C to rt, 3 d; 89% 3 Boc Cbz C 2 Bn H 2 (1atm), Pd/C (5% w/w), MeH rt, overnight BocH H BocH Boc Boc Fmoc-Su (1.5 eq), H a 2 C 3 (2.0 eq), DMF/H 2 C 2 H C 2 H 0 C to rt, 2 h; 24% H Fmoc 65 17
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80 Cl Boc H 2 (1.7 eq), 2 H Tf 2 (1.1 eq), Tf ah (4.0 eq) Hünig's base (1.1 eq), DCM H 2 H 2 0 C to rt, 22 h; BocH HBoc BocH HBoc -78 C to -20 C, 3.5 h; 66 55% 67 75% 18
81 10 Θ /10 3 deg cm 2 dmol PPII conformation Min 206 nm Max 226 nm ZPZ ZPZ ZPZ (24) PPP ZZZ ZZZ (29) λ [nm]
82 a) 10 b) Θ /10 3 deg cm 2 dmol λ [nm] ZPZ ZPZ ZPZ (24) UPU UPU UPU (21) PPP PPP PPP (50) Θ /10 3 deg cm 2 dmol zpz zpz zpz (27) 20 xpx xpx xpx (28) 30 ZPZ ZPZ ZPZ (24) XPX XPX XPX (26) λ [nm]
83 a) 5 b) Θ /10 3 deg cm 2 dmol αβ 0 λ [nm] RRR RRR RR (45) Tat(48 60) (42) Penetratin (43)
84 Hela MCF-7 PC-3 HT-29
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102 A B C D A B C D
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104 .2 7 %!! ) $&! $ "! # "! + ) 15 2-,) # $ #!!!!! %! + # " # $ $! & 0).)1).)., % # $ " #,) (! # * * * * * / +, ,'! * # 0001/ +, " $ +,) (! # * * * * * / +, ,'! * # 0001/ +, " $ +,) (! # * * 4* 036 +,'! * # 0001/ +, " $ +,) 4/ / +,.2 7.
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109 Tat(48-60) CF-G-RKK-RRQ-RRR-PPQ-CH2 (42) CF-G-RRR-RRR-RR-CH2 (45) mau Control mau Control min min mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
110 CF-G-ZZZ-ZZZ-PPP-CH2 (30) CF-G-ZZZ-ZZZ-ZZ-CH2 (39) mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
111 CF-G-PPP-PPP-PPP-CH2 (50) CF-G-ppp-ppp-ppp-CH2 (52) mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
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113 Tat(48-60) CF-G-RKK-RRQ-RRR-PPQ-CH2 (42) CF-G-RRR-RRR-RR-CH2 (45) mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
114 CF-G-ZZZ-ZZZ-PPP-CH2 (30) CF-G-ZZZ-ZZZ-ZZ-CH2 (39) mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
115 CF-G-PPP-PPP-PPP-CH2 (50) CF-G-ppp-ppp-ppp-CH2 (52) mau 0 min mau 0 min min min mau 1 h mau 1 h min min mau 48 h mau 48 h min min
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117 Mitochondrial dehydrogenase Br S ADH AD+ H S MTT pale yellow Formazan purple Mitochondrion of a viable cell
118 Cell Viability (%)
119 Cell Viability (%)
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121 ± ± ± a) Hemolysis (%) b) Hemolysis (%)
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125 a) siren Transfection via CPPs b) c) psicheck-2 vector Transfection via jetpei Beetle luciferin Celenterazine
126 a) H S S CH + ATP + 2 Recombinant Firefly Luciferase Mg 2+ S S + AMP + PP i + C 2 Beetle Luciferin hv xyluciferin b) H H H Renilla Luciferase + 2 hv H H H + C 2 Coelenterazine Coelenteramide
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129 3 * Me BocH * Me X H 3 * Me BocH Boc H * Me H 2 X H 2 H * Me 7 8 X = CF 3 C 2 9 X = Cl X = CF 3 C 2 12 X = Cl 13
130 H 3 H 3 H 3 H 3 H H 3 3
131 3 a) Methansulfonic acid, a) Et H 3, MsCl, Et 3 3, PPh 3, DIAD, DCM, rt, 2h toluene, 70 C, 5 h C 2 Me C 2 Me b) a C 2 Me 3, DMF, b) a 3, DMF, Boc 80 C, 26 h; 95% 80 C, 17 h; 95% Boc Boc 56S 55 56R
132 3 * Boc 56R 56S Lindlar cat., Boc 2, H 2, C 2 Me HCl/dioxane (4 M) rt, 5 h; 69S: quant.; 69R: 87% BocH * 3 H 2 Cl C 2 Me Ac 2, Et 3, DCM rt, 4 h a) DCM/TFA 3:2, 1 h, rt or b) HCl in dioxane, 5 h, rt MeH, rt, 7 h C 2 Me X = CF 3 C 2 : 9S: 85%; 8S: quant.; 9R: 85% 8R: quant. X = Cl: 10S: quant.; 10R: quant. Tf BocH Boc BocH HBoc H a) DCM/TFA 1:1, 1.5 h, rt or 18 b) HCl in dioxane, 5 h, rt Et 3, DCM, rt, 5 h C 2 Me X = CF 3 C 2 : 12S: quant.; 11S: quant.; 12R: quant. 11R: 94% X = Cl: 13S: 70%; 13R: 73% * * 7S: 95%; 7R: 71% 3 H 3 H 2 H * * * X H 2 C 2 Me C 2 Me X C 2 Me
133 ψ
134 a) b) (R) Hγ X i Ψ ~145 C i C i-1 n π* stabilization repulsion X (S) Hγ CH3 Ψ ~145 C(4)-exo conformation X = e. g. F or 3 C(4)-endo conformation
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136 a) H-bonding b) H Y CH3 Ψ ~145 n π* Hγ stabilization
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141 20 20 Θ /10 3 deg cm 2 dmol R Θ /10 3 deg cm 2 dmol S λ [nm] λ [nm] 30 73R 2R 2S 73S [Θ] (10 3 deg cm 2 dmol -1 ) Wavelength (nm) Wavelength (nm)
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146 π
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149 H Cl H 2 Me
150 H Boc Me
151 3 Boc Me
152 3 Boc H
153 H 2 H Cl 3
154 3 Fmoc H
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156 3 Boc Me
157
158 3 Boc H
159 H 2 H Cl 3
160 3 Fmoc H
161 H Cbz C 2 H
162 H Cbz C 2 Bn
163 Ms Cbz C 2 Bn
164 3 Cbz C 2 Bn
165 H 2 Cbz C 2 Bn
166 BocH H Boc C 2 Bn Cbz
167 BocH H Boc C 2 H H
168 BocH H Boc C 2 H Fmoc
169 BocH H HBoc
170 BocH Tf HBoc
171 3 Cl H 2 Me
172 3 Me
173 3 Cl H 2 Me
174 3 Me
175 BocH Me
176 BocH Me
177 CF 3 C 2 H 3 Me
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179 Me CF 3 C 2 H 3
180 Cl H 3 Me
181 Me Cl H 3
182 BocH H Boc Me
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184 BocH Boc H Me
185 H 2 H CF 3 C 2 H 2 Me
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187 H 2 H CF 3 C 2 H 2 Me
188 H 2 H Cl H 2 Me
189 H 2 H Cl H 2 Me
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203 = = = =
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233 Θ /10 3 deg cm 2 dmol PPP PPP PPP PPP PPP Θ /10 3 deg cm 2 dmol ppp ppp ppp ppp ppp λ [nm] λ [nm]
234 BocH * Me
235 CF 3 C 2 H 3 * Me
236 Cl H 3 * Me
237 Boc H * BocH Me
238 CF 3 C 2 H 2 H 2 H * Me
239 Cl H 2 H 2 H * Me
240 a) b) c)
241 a)
242
Azidoproline containing Helices Stabilization of the Polyproline II Structure by a Functionalizable Group
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