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«A template-directed synthetic approach to halogen-bridged mixed-valence platinum complexes on artificial peptides in solution a Kentaro Tanaka,a,b ...»

-- [ Page 1 ] --

Electronic Supplementary Information for Dalton Transactions

This journal is © The Royal Society of Chemistry 2007

Electronic Supplementary Information

A template-directed synthetic approach to halogen-bridged mixed-valence platinum

complexes on artificial peptides in solution

a

Kentaro Tanaka,a,b Kenji Kaneko,a Yusuke Watanabea and Mitsuhiko Shionoya*

a

Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku,

Tokyo 113-0033, Japan.

Fax: +81 3 5841 8061; Tel: +81 3 5841 8061; E-mail: shionoya@chem.s.u-tokyo.ac.jp b Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8602, Japan.

Fax: +81 52 789 2940; Tel: +81 52 789 2940; E-mail: kentaro@chem.nagoya-u.ac.jp Contents

1. General experimental methods ···· page S2 2. Syntheses of the Pt complex-pendant peptides ([1a-d(Pt(IV)Br2 (en))n ](RSO3 )2n and [1a-d(Pt(II)(en))n ](RSO3 )2n : (n = 2, 3, 9, 10) and mononuclear Pt complexes (R = (C 12 H25 OCH2 )2 CHO(CH2 )3 -) ···· page S3

3. Photometric titration spectra of [1b(Pt(IV)Br2 (en))3 ](RSO3 )6 with [1a(Pt(II)(en))2 ](RSO3 )4 (Fig. S1) ···· page S21

4. Photometric titration spectra of [1d(Pt(IV)Br2 (en))10 ](RSO3 )20 with [1c(Pt(II)(en))9 ](RSO3 )18 (Fig.

S2) ···· page S22

5. 1 H NMR titration spectra of [1a(Pt(IV)Br2 (en))2 ](RSO3 )4 with [Pt(II)(en)2 ](RSO3 )2 (Fig. S3) ···· page S23

6. References ···· page S24 S1 Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2007 General experimental methods All reactions were carried out in oven dried glasswares with commercial dehydrated solvents (Wako Pure Nα-t-Boc-β-amino-L-alanine,1 1-amino-11-azido-3,6,9-trioxaundecane,2 Chemical Industries).

1,3-bis-dodecyloxy-propan-2-ol,3 [Pt(II)Br2(en)],4 [Pt(II)(en)2]Br24 and [Pt(IV)Br2(en)2]Br24 were prepared according to previously published procedures. 0.5 M NH3 /1,4-dioxane was purchased from Sigma-Aldrich.

40% Methylamine/methanol, 4 M HCl/1,4-dioxane, N-methyl morpholine and 1-ethyl-3-(3’-dimethylaminopropyl)-carbodiimide·HCl were purchased from Tokyo Chemical Industry.

9-fluorenylmethyloxycarbonyl-N-hydroxysuccinimide (Fmoc-OSu), Rink Amide AM-resin and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HBTU) were purchased from Novabiochem. Reverse-phase-high performance liquid chromatography (RP-HPLC) eluents were purchased from Kanto Chemical. All other reagents were purchased from Wako Pure Chemical Industries and were used without further purification. Column chromatography was performed using Wakogel C-300 silica gel (Wako Pure Chemical Industries). Reverse-phase column chromatography was performed using Wakogel 50C18 silica gel (Wako Pure Chemical Industries). Thin-layer chromatography was performed on silica gel 60 F254 1.0554 (Merck). Anion exchange column chromatography was carried out on Amberlite IRA-400 (Organo). 1H, 13 C and 1H-1H COSY NMR spectra were recorded on a Bruker DRX 500 (500 MHz 1H; 125.65 MHz 13

C) spectrometer. The spectra are referenced to either Me4Si in acetonitrile-d3, chloroform-d, dichloromethane-d2 and methanol-d4 or the signal of the solvent (acetonitrile-d3; 1.94 ppm). Chemical shifts (δ) are reported in ppm; multiplicities are indicated by: s (singlet), d (doublet), t (triplet), dd (double doublet), dt (double triplet), m (multiplet), br (broad). Coupling constants, J, are reported in Hz. Electrospray ionization-time-of-flight (ESI-TOF) mass spectra were recorded on a Micromass LCT spectrometer. RP-HPLC was carried out on a TOSOH instrument equipped with a solvent delivery pump (preparative; CCPP-M, analysis; CCPM-II), an UV-vis absorbance detector (UV-8020) and a temperature controller (CO-8020) with Wakopak Navi C18-5 (preparative; 20 × 250 mm, analysis; 4.6 × 250 mm) columns and eluents specialized in HPLC. Gel permeation chromatography (GPC) was performed on a recycling preparative HPLC (Japan Analytical Industry; LC-928R/U) with an UV-vis absorbance detector (S-3740) with a JAIGEL-2H-40 (40 × 600 mm) column. UV-vis absorption spectra were recorded on a Hitachi U-3500 spectrometer equipped with a Peltier thermoelectric temperature control unit.

–  –  –

Syntheses of the Pt complex-pendant peptides ([1a-d(Pt(IV)Br2(en))n](RSO3)2n and [1a-d(Pt(II)(en))n](RSO3)2n: (n = 2, 3, 9, 10) and mononuclear Pt complexes (R = (C12 H25 OCH2 )2 CHO(CH2 )3 -) The building block 1 of the template peptides was prepared according to Scheme S1.

–  –  –

Pt complex-pendant peptides ([1a-d(Pt(II)(en))n ](RSO3 )2n and [1a-d(Pt(IV)Br2 (en))n ](RSO3 )2n : (n = 2, 3, 9, 10)) were prepared according to Scheme S2.

Scheme S2 A synthetic route to Pt complex-pendant peptides ([1a-d(Pt(II)(en))n](RSO3)2n and [1a-d(Pt(IV)Br2(en))n](RSO3)2n).

A sodium dialkylsulfonate, RSO3Na, was synthesized according to Scheme S3.

–  –  –

Synthesis of (S)-N,N’-di-t-Boc-2,3-diaminopropanol 2 To a solution of Nα-t-Boc-β-amino-L-alanine (6.60 g, 32.3 mmol) and NaHCO3 (2.72 g, 32.3 mmol) in THF/water (1:1, 66 cm3 ) was added dropwise a solution of di-t-butyl-dicarbonate (Boc2 O, 7.42 cm3,

32.3 mmol) in THF (50 cm3 ) at 0 °C under a nitrogen atmosphere. After stirring for 15 h at room temperature, THF was removed under reduced pressure and dried in vacuo. 5% KHSO4 aqueous solution (250 cm3 ) was added to the residue, and di-Boc compound was extracted with ethyl acetate (3 × 250 cm3 ). The combined organic layer was washed with 5% KHSO4 aqueous solution (100 cm3 ) and water (100 cm3 ). The organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure and dried in vacuo. To a solution of the residue (10.4 g) in THF (170 cm3 ) was added dropwise N-methyl morpholine (3.76 cm3, 34.2 mmol) and isopropyl chloroformate (3.92 cm3,





34.2 mmol) at -15 °C under a nitrogen atmosphere. After stirring for 15 min at -15 °C, sodium tetrahydroborate (1.94 g, 51.2 mmol) was carefully added to the mixture and stirred for 45 min at room temperature. The reaction was quenched by adding methanol (100 cm3 ), and then the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (300 cm3 ) and washed with 5% KHSO4 /brine (3 × 150 cm3 ) and water (2 × 100 cm3 ). The organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure and dried in vacuo. The crude material was chromatographed on silica gel with CH2 Cl2 /methanol (100:0 - 99:1) to give compound 2 (5.50 g, 59% (3 steps)) as a colorless solid (Found: C, 53.59; H, 9.02; N, 9.50.

C 13 H26 N2 O5 requires C, 53.78; H, 9.02; N, 9.65); Rf 0.50 (chloroform/methanol/acetic acid (90:10:1));

δH(500 MHz; CDCl3 ; Me4 Si) 5.14 (d, J = 8.2 Hz, 1H, Boc-NHCH-), 5.06 (br, 1H, Boc-NHCH2 -), 3.75-3.72 (m, 1H, -OH, D2 O exchangable), 3.69-3.67 (m, 1H, -CHHOH), 3.57 (br, 1H, methine), 3.51 (br, 1H, -CHHOH), 3.34-3.19 (m, 2H, Boc-NHCH2 -), 1.44 (s, 9H, t-Bu), 1.44 (s, 9H, t-Bu); δC(125 MHz; CDCl3 ; Me4 Si) 157.9, 155.9, 80.5, 79.8, 61.7, 52.4, 40.3, 28.5, 28.4; m/z (ESI-TOF) 313.23 (M + Na+. C 13 H26 N2 NaO5 requires 313.18).

–  –  –

Synthesis of (S)-2,3-bis(phthalimido)propanol 3 A solution of compound 2 (5.00 g, 17.2 mmol) in 4 M HCl/1,4-dioxane (25 cm3, 100 mmol) was stirred for 11 h at room temperature. After the solvent was evaporated, the residue was dissolved in THF (60 cm3 ) and then triethylamine (3.48 cm3, 34.4 mmol) and phthalic anhydride (5.10 g, 34.4 mmol) were added to the solution. The reaction mixture was stirred for 3 h at room temperature, and then heated at reflux for 10 h at 80 °C. The solvent was removed under reduced pressure and 5% KHSO4 aqueous solution (100 cm3 ) was added to the residue, which was extracted with ethyl acetate (3 × 100 cm3 ) and the combined organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude solid was washed with cooled ethanol to afford compound 3 (3.85 g) as a colorless solid. The resulting filtrate was recrystallized with ethanol (30 cm3 ) to afford compound 3 (0.74 g) as colorless needles (4.59 g, 76% in total (2 steps)) (Found: C, 64.80; H, 4.31; N,

7.79. C19 H14 N2 O5 requires C, 65.14; H, 4.03; N, 8.00); Rf 0.80 (n-butanol/pyridine/acetic acid/water (4:1:1:2)); δH(500 MHz; CDCl3 ; Me4 Si) 7.82-7.67 (m, 8H, 2 × phthalimide), 4.68-4.63 (m, 1H, methine), 4.34 (dd, J = 14.6, 8.5 Hz, 1H, -NCHHCH-), 4.14 (dd, J = 7.0, 5.3 Hz, 2H, -CH2 OH), 4.09 (dd, J = 14.6, 3.5 Hz, 1H, -NCHHCH-), 3.44 (t, J = 7.0 Hz, 1H, -OH, D2 O exchangeable); δ C(125 MHz; CDCl3 ; Me4 Si) 169.1, 168.5, 134.4, 134.3, 131.9, 131.7, 123.6, 123.6, 61.8, 52.8, 37.3; m/z (ESI-TOF) 373.10 (M + Na+. C 19 H14 N2 NaO5 requires 373.08).

Synthesis of methyl (S)-5,6-bis(phthalimido)-3-oxahexanoate 4 To a solution of compound 3 (767 mg, 2.19 mmol) in THF (10 cm3 ) was added sodium hydride (in oil (60%), 350 mg, 8.75 mmol) at room temperature. After stirring for 5 min at room temperature, methyl

–  –  –

bromoacetate (0.83 cm3, 8.75 mmol) was added and then stirred for 48 h at room temperature. The mixture was poured into 10 cm3 of ice water and 5% KHSO4 /brine (50 cm3 ) was added, which was extracted with ethyl acetate (3 × 50 cm3 ). The combined organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography with n-hexane/ethyl acetate (3:1) to obtain compound 4 (735 mg, 79%) as a colorless syrup; Rf 0.74 (chloroform/methanol/acetic acid (90:10:1)); δH(500 MHz; CDCl3 ;

Me4 Si) 7.82-7.67 (m, 8H, 2 × phthalimide), 4.80-4.75 (m, 1H, methine), 4.31 (dd, J = 14.3, 8.4 Hz, 1H,

-NCHHCH-), 4.18 (dd, J = 14.3, 8.4 Hz, 1H, -CHCHHO-),, 4.13 (dd, J = 10.2, 6.0 Hz, 1H,

-CHCHHO-), 4.13 (s, 2H, -OCH2 CO-), 4.12 (dd, J = 14.3, 4.0 Hz, 1H, -NCHHCH-), 3.69 (s, 3H, methyl); δC(125 MHz; CDCl3 ; Me4 Si) 173.4, 168.5, 168.3, 134.3, 134.3, 131.8, 131.8, 123.6, 123.6, 69.2, 68.0, 50.5, 37.2, 31.1; m/z (ESI-TOF) 445.18 (M + Na+. C 22 H18 N2 NaO6 requires 445.10).

Synthesis of (S)-5,6-bis(phthalimido)-3-oxahexanoic acid 5

To a solution of compound 4 (1.05 g, 2.49 mmol) in formic acid (25 cm3 ) was added methane sulfonic acid (0.16 cm3, 2.49 mmol) at room temperature. After stirring for 16 h at 80 °C, the mixture was poured into 150 cm3 of water, and then 5 was extracted with chloroform (3 × 150 cm3 ). The combined organic layer was washed with brine (100 cm3 ) and dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography with chloroform/methanol (99:1) to afford compound 5 (0.86 g, 85%) as a colorless syrup; Rf 0.45 (chloroform/methanol/acetic acid (90:10:1)); δH(500 MHz; CDCl3 ; Me4 Si) 7.82-7.69 (m, 8H, 2 × phthalimide), 4.79-4.74 (m, 1H, methine), 4.33 (dd, J = 14.3, 8.0 Hz, 1H, -NCHHCH-), 4.20-4.11 (m, 5H, -NCHHCH-, -CHCH2 O-, -OCH2 CO-); δC (125 MHz; CDCl3 ; Me4 Si) 174.1, 168.5, 168.3, 134.3, 134.3, 131.8, 131.8, 123.6, 123.6 69.2, 67.9, 50.5, 37.2; m/z (ESI-TOF) 431.16 (M + Na+.

C 21 H16 N2 NaO7 requires 431.09).

–  –  –

Synthesis of (S)-N,N’-di-t-Boc-5,6-diamino-3-oxahexanoic acid 6 Compound 5 (850 mg, 2.08 mmol) was dissolved in 40% methylamine/methanol (10 cm3, 253 mmol) and stirred for 8 h at room temperature. After removal of the solvent and dried in vacuo, the residue was dissolved in water (100 cm3 ) and washed with chloroform/THF (4:1, 8 × 100 cm3 ). The solvent of the aqueous layer was removed under reduced pressure and dried in vacuo. To a solution of the crude material (362 mg) in THF/water (1:1, 10 cm3 ) was added NaHCO3 (350 mg, 4.16 mmol) and Boc2 O (1.00 cm3, 4.16 mmol). After stirring for 11 h at room temperature, THF was removed under reduced pressure, and then 5% KHSO4 aqueous solution (30 cm3 ) was added, which was extracted with ethyl acetate (3 × 40 cm3 ). The combined organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography with chloroform/methanol (100:0 - 99:1) to obtain compound 6 (584 mg, 81% (2 steps)) as a colorless syrup; Rf 0.72 (n-butanol/pyridine/acetic acid/water (4:1:1:2)); δH(500 MHz;

CDCl3 ; Me4 Si) 5.35-5.20 (m, 2H, Boc-NHCH-, Boc-NHCH2 -), 4.18-4.05 (m, 2H, -OCH2 CO-), 3.81 (br, 1H, methine), 3.67-3.65 (m, 1H, -CHCHHO-), 3.55-3.52 (m, 1H, -CHCHHO-), 3.41-3.32 (m, 2H, Boc-NHCH2 -), 1.44 (m, 18H, 2 × Boc); δC(125 MHz; CDCl3 ; Me4 Si) 172.9, 157.0, 156.1, 80.0, 79.8, 71.4, 68.3, 50.7, 41.6, 28.4; m/z (ESI-TOF) 371.19 (M + Na+. C 15 H28 N2 NaO7 requires 371.18).

Synthesis of N-(11-azido-3,6,9-trioxaundecyl)glycine t-butyl ester 7

To a solution of 1-amino-11-azido-3,6,9-trioxaundecane (19.5 g, 89.3 mmol) and triethylamine (24.8 cm3, 179 mmol) in CH2 Cl2 (200 cm3 ) was added dropwise within 1 h a solution of t-butyl bromoacetate (13.1 cm3, 89.3 mmol) in CH2 Cl2 (300 cm3 ) at 0 °C with a dropping funnel under a nitrogen atmosphere. After stirring for 17 h at room temperature, the mixture was washed with brine (3 × 500 cm3 ). The organic layer was dried over anhydrous Na2 SO4 and the solvent was removed under reduced pressure and dried in vacuo. The crude material (31.2 g) was purified by silica gel column chromatography with chloroform/methanol (50:1 - 20:1) to obtain compound 7 (23.5 g, 79%) as a yellow-brown solution; Rf 0.61 (n-butanol/pyridine/water (4:1:2)); δH(500 MHz; CDCl3 ; Me4 Si) S8 Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2007 3.70-3.63 (m, 10H, N3 CH2 CH2 O-, -OCH2 CH2 OCH2 CH2 O-), 3.59 (t, J = 5.6 Hz, 2H, -NHCH2 CH2 -), 3.40 (t, J = 5.1 Hz, 2H, N3 CH2 -), 3.33 (m, 2H, -NHCH2 CO-), 2.80 (t, J = 5.6 Hz, 2H, -NHCH2 CH2 -), 1.47 (s, 9H, t-Bu); δC(125 MHz; CDCl3 ; Me4 Si) 171.5, 81.0, 70.7, 70.7, 70.6, 70.6, 70.3, 70.0, 51.7, 51.7, 50.6, 48.7.



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