Supporting Information
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- Νάρκισσα Καλύβας
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2014 A Family of Click Nucleosides for Metal-Mediated Base Pairing: Unravelling the Principles of Highly Stabilizing Metal-Mediated Base Pairs Tim Richters, [a] Olga Krug, [b] Jutta Kçsters, [a] Alexander Hepp, [a] and Jens Müller* [a] chem_ _sm_miscellaneous_information.pdf
2 Figure S1: Molecular structure of the cation of [Pd(BnTriPyr) 2 ]Cl 2 2 H 2 O viewed from two different orientations.
3 Table S1. Melting temperature T m ( C) of duplex I in the absence of Ag(I). [a] X = Imi X = TriTri X = TriPyr X = TriPy Y = Imi Y = TriTri Y = TriPyr Y = TriPy [a] Conditions: 1 μm oligonucleotide duplex, 150 mm NaClO 4, 5 mm MOPS (ph 6.8), 1 μm AgNO 3. The estimated standard deviation of T m amounts to 1 C. Table S2. Melting temperature T m ( C) of duplex I in the presence of one equivalent of Ag(I). [a] X = Imi X = TriTri X = TriPyr X = TriPy Y = Imi Y = TriTri Y = TriPyr Y = TriPy [a] Conditions: 1 μm oligonucleotide duplex, 150 mm NaClO 4, 5 mm MOPS (ph 6.8), 1 μm AgNO 3. The estimated standard deviation of T m amounts to 1 C.
4 Characterization of toluoyl-protected nucleosides TolTriTri: Yield: 3.34 g, 6.65 mmol, 83%, white solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.14 (s, 1 H, H5*), 7.93 (d, 2 H, H meta (Tol)), 7.90 (s, 1 H, H3*), 7.84 (d, 2 H, H meta (Tol)), 7.82 (s, 1 H, H5), 7.24 (m, 4 H, H ortho (Tol)), 6.45 (t, 1 H, H1 ), 5.75 (d, 1 H, H3 ), 5.39 (m, 2 H, CH 2 ), 4.65 (q, 1 H, H4 ), 4.61 (dd, 2 H, H5, H5 ), 3.19 (dt, 1 H, H2 or H2 ), 2.86 (ddd, 1 H, H2 or H2 ), 2.43 (s, 3 H, CH 3 (Tol)), 2.41 (s, 3 H, CH 3 (Tol)) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (C=O), (C=O), (C3*), (Tol), (Tol), (C4), (C5*), (Tol), (Tol), (Tol), (Tol), (Tol), (C5), (C5), 89.1 (C1 ), 83.9 (C4 ), 74.7 (C3 ), 63.9 (C5 ), 44.8 (CH 2 ), 38.3 (C2 ), 21.7 (CH 3 (Tol)) ppm. C 26 H 26 N 6 O 5 (502.52): calcd. C 62.14, H 5.20, N 16.72; found C 62.17, H 5.21, N Mass (m/z) for (M+Na) + : calcd ; found TolTriPyr: 3.06 g, 6.01 mmol, 88%, white solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.92 (d, 2 H, H meta (Tol)), 7.82 (s, 1 H, H5), 7.65 (d, 2 H, H ortho (Tol)), 7.46 (m, 2 H, H5*, H3*), 7.26 (m, 2 H, H ortho (Tol)), 7.19 (m, 2 H, H ortho (Tol)), 6.44 (dd, 1 H, H4*), 6.20 (t, 1 H, H1 ), 5.60 (dt, 1 H, H3 ), 5.43 (d, 2 H, CH 2 ), 4.74 (m, 1 H, H4 ), 4.59 (dd, 2 H, H5, H5 ), 3.15 (m, 1 H, H2 or H2 ), 3.00 (m, 1 H, H2 or H2 ), 2.42 (s, 3 H, CH 3 (Tol)), 2.40 (s, 3 H, CH 3 (Tol)) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (C=O), (C=O), (Tol), (Tol), (C4), (C3*), (Tol), (Tol), (C5*), (Tol), (Tol), (Tol), (C5), (C4*), 88.9 (C1 ), 83.7 (C4 ), 74.8 (C3 ), 63.9 (C5 ), 47.3 (CH 2 ), 38.1 (C2 ), 21.7 (CH 3 ) ppm. C 27 H 27 N 5 O 5 (501.54): calcd. C 64.66, H 5.43, N 13.96; found C 64.96, H 5.34, N Mass (m/z) for (M+Na) + : calcd ; found TolTriPy: 1.23 g, 2.47 mmol, 74%, white solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.55 (s, 1 H, H2*), 8.40 (d, 1 H, H5), 8.12 (d, 1 H, H5*), 7.96 (d, 2 H, H meta (Tol)), 7.94 (d, 2 H, H meta (Tol)), 7.77 (t, 1 H, H4*), 7.26 (d, 2 H, H ortho (Tol)), 7.23 (d, 1 H, H3*), 7.15 (m, 2 H, H ortho (Tol)), 6.54 (t, 1 H, H1 ), 5.80 (m, 1 H, H3 ), 4.68 (m, 1 H, H4 ), 4.60 (m, 2 H, H5, H5 ), 3.25 (m, 1 H, H2 or H2 ), 2.89 (ddd, 1 H, H2 or H2 ), 2.44 (s, 3 H, CH 3 (Tol)), 2.36 (s, 3 H, CH 3 (Tol)) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (C=O), (C=O), (C6*), (C2*), (C4*), (Tol), (Tol), (C4), (Tol), (Tol), (Tol), (Tol), (Tol), (Tol), (C5*), (C3*), (C5), 88.9 (C1 ), 83.6 (C4 ), 74.7 (C3 ), 63.9 (C5 ), 38.2 (C2 ), 21.7 (CH 3 (Tol)) ppm. C 28 H 26 N 4 O 5 (498.52): calcd. C 67.46, H 5.26, N 11.24; found C 67.78, H 5.32, N Mass (m/z) for (M+Na) + : calcd ; found
5 Characterization of free nucleosides NucTriTri: 1.68 g, 6.29 mmol, 95%, white solid. 1 H NMR (400 MHz, CD 3 OD): δ = 8.59 (s, 1 H, H5*), 8.29 (s, 1 H, H3*), 8.01 (s, 1 H, H5), 6.44 (t, 1 H, H1 ), 5.60 (s, 2 H, CH 2 ), 4.56 (q, 1 H, H3 ), 4.05 (q, 1 H, H4 ), 3.74 (dd, 1 H, H5 or H5 ), 3.65 (dd, 1 H, H5 or H5 ), 2.79 (m, 1 H, H2 or H2 ), 2.54 (m, 1 H, H2 or H2 ) ppm. 13 C NMR (100 MHz, CD 3 OD): δ = (C3*), (C5*), (C4), (C5), 90.3 (C1 ), 89.7 (C4 ), 72.1 (C3 ), 63.1 (C5 ), 45.4 (CH 2 ), 41.7 (C2 ) ppm. C 10 H 14 N 6 O 3 (266.26): calcd. for M 0.25 H 2 O: C 44.34, H 5.40, N 31.05; found C 44.10, H 5.19, N Mass (m/z) for (M+Na) + : calcd ; found NucTriPyr: 711 mg, 2.68 mmol, 90%, white solid. 1 H NMR (400 MHz, D 2 O, pd 7.1): δ = 8.13 (s, 1 H, H5), 7.75 (s, 1 H, H5*), 7.58 (s, 1 H, H3*), 6.45 (t, 1 H, H1 ), 6.38 (dt, 1 H, H4*), 5.46 (s, 2 H, CH 2 ), 4.59 (q, 1 H, H3 ), 4.13 (q, 1 H, H4 ), 3.75 (dd, 1 H, H5 or H5 ), 3.62 (dd, 1 H, H5 or H5 ), 2.83 (m, 1 H, H2 or H2 ), 2.60 (m, 1 H, H2 or H2 ) ppm. 13 C NMR (100 MHz, D 2 O, pd 7.1): δ = (C5*), (C3*), (C4), (C5), (C4*), 88.6 (C1 ), 87.5 (C4 ), 70.5 (C3 ), 61.4 (C5 ); 45.9 (CH 2 ), 39.2 (C2 ) ppm. C 11 H 15 N 5 O 3 (265.27): calcd.: C 49.81, H 5.70, N 26.40; found C 49.70, H 5.50, N Mass (m/z) for (M+Na) + : calcd ; found NucTriPy: 510 mg, 1.94 mmol, 95%, white solid. 1 H NMR (400 MHz, D 2 O, pd 6.6): δ = 8.34 (s, 1 H, H2*), 8.32 (s, 1 H, H5), 7.76 (m, 1 H, H5*), 7.68 (m, 1 H, H4*), 7.27 (m, 1 H, H3*), 6.45 (t, 1 H, H1 ), 4.62 (dt, 1 H, H3 ), 4.17 (dt, 1 H, H4 ), 3.79 (dd, 1 H, H5 or H5 ), 3.67 (dd, 1 H, H5 or H5 ), 2.84 (ddd, 1 H, H2 or H2 ); 2.64 (ddd, 1 H, H2 or H2 ) ppm. 13 C NMR (100 MHz, D 2 O, pd 6.6): δ = (C6*), (C2*), (C4*), (C4), (C5), (C5*), (C3*), 88.7 (C1 ), 87.8 (C4 ), 70.7 (C3 ), 61.5 (C5 ), 39.4 (C2 ) ppm. C 12 H 14 N 4 O 3 (262.26): calcd. for M 1.25 H 2 O: C 50.34, H 5.87, N 19.57; found C 50.37, H 5.38, N Mass (m/z) for (M+Na) + : calcd ; found
6 Characterization of DMT-protected nucleosides DMTTriTri: 3.14 g, 5.53 mmol, 88%, white foam. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.03 (s, 1 H, H5), 7.84 (d, 2 H, H3*, H5*), 7.33 (m, 2 H, DMT), (m, 7 H, DMT), 6.79 (d, 4 H, DMT), 6.32 (t, 1 H, H1 ), 5.27 (d, 2 H, CH 2 ), 4.63 (m, 1 H, H3 ), 4.13 (m, 1 H, H4 ), 3.77 (s, 6 H, OCH 3 ), 3.31 (m, 2 H, H5, H5 ), 2.80 (m, 1 H, H2 or H2 ), 2.53 (m, 1 H, H2 or H2 ) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (DMT), (C3*), (C5*), (DMT), (C4), (DMT), (DMT), (DMT), (DMT), (DMT), (DMT), (DMT), (DMT), (C5), (DMT), 88.8 (C1 ), 86.6 (C4 ), 70.8 (C3 ), 63.2 (C5 ), 55.2 (OCH 3 ), 44.6 (CH 2 ), 40.8 (C2 ) ppm. C 31 H 32 N 6 O 5 (568.62): calcd. for M 0.66 H 2 O: C 64.13, H 5.79, N 14.47; found C 64.58, H 5.93, N Mass (m/z) for (M+Na) + : calcd ; found DMTTriPyr: 1.35 g, 2.37 mmol, 62%, white foam. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.60 (d, 1 H, H5*), 7.86 (s, 1 H, H5), 7.51 (m, 2 H, DMT), 7.40 (d, 2 H, DMT), (m, 5 H, DMT), 6.20 (d, 1 H, H3*), 6.82 (d, 4 H, DMT), 6.35 (d, 1 H, H4*), 6.26 (t, 1 H, H1 ), 5.44 (s, 2 H, CH 2 ), 4.45 (s, 1 H, H3 ), 4.35 (s, 1 H, H4 ), 3.78 (s, 6 H, OCH 3 ), 3.30 (dd, 1 H, H5 or H5 ), 3.13 (dd, 1 H, H5 or H5 ), 2.92 (dt, 1 H, H2 or H2 ), 2.34 (m, 1 H, H2 or H2 ) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (DMT), (DMT), (DMT), (DMT), (DMT), (C3*), (C5*), (C4), (DMT), (DMT), (DMT), (DMT), (DMT), (C5), (DMT), (DMT), (C4*), 89.8 (C1 ), 86.3 (C4 ), 72.4 (C3 ), 63.9 (C5 ), 55.2 (OCH 3 ), 47.2 (CH 2 ), 41.0 (C2 ) ppm. C 32 H 33 N 5 O 5 (567.63): calcd. C 67.71, H 5.86, N 12.34; found C 67.57, H 5.72, N Mass (m/z) for (M+Na) + : calcd ; found DMTTriPy: 321 mg, 0.57 mmol, 26%, white foam. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.53 (ddd, 1 H, H2*), 8.31 (s, 1 H, H5), 8.03 (dt, 1 H, H5*), 7.71 (td, 1 H, H4*), 7.36 (m, 2 H, DMT), (m, 7 H, DMT), 7.13 (m, 1 H, H3*), 6.74 (d, 4 H, DMT), 6.38 (t, 1 H, H1 ), 5.27 (d, 2 H, H6*), 4.58 (m, 1 H, H3 ), 4.15 (m, 1 H, H4 ), 3.69 (s, 6 H, OCH 3 ), 3.30 (m, 1 H, H5 or H5 ); 3.23 (m, 1 H, H5 or H5 ), 2.85 (m, 2 H, H2, H2 ) ppm. 13 C NMR (100 MHz, CDCl 3 ): δ = (DMT), (C6*), (C2*), (DMT), (C4*), (DMT), (DMT), (C4), (DMT), (DMT), (DMT), (DMT), (C5), (C5*), (C3*), (DMT), 88.6 (DMT), 86.6 (C1 ), 86.3 (C4 ), 71.2 (C3 ), 63.9 (C5 ), 55.1 (OCH 3 ), 40.6 (C2 ) ppm. C 33 H 32 N 4 O 5 (567.63): calcd. for M H 2 O 0.5 NEt 3 : C 68.28, H 6.61, N 9.95; found C 68.40, H 6.57, N Mass (m/z) for (M+Na) + : calcd ; found
7 Characterization of orthogonal protected nucleosides PhosTriTri: 887 mg, 1.15 mmol, 90%, pale yellowish oil. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.96 (s, 1 H, H5), 7.79 (s, 2 H, H5*, H3*), 7.27 (m, 2 H, DMT), (m, 7 H, DMT), 6.72 (m, 4 H, DMT), 6.28 (t, 1 H, H1 ), 5.22 (m, 2 H, CH 2 ), 4.67 (m, 1 H, H3 ), 4.16 (m, 1 H, H4 ), (m, 8 H, OCH 3, CH(CH 3 ) 2 ), 3.49 (m, 2 H, CH 2 CN), 3.23 (m, 2 H, H5, H5 ), 2.78 (m, 1 H, H2 or H2 ), 2.61 (m, 1 H, H2 or H2 ), 2.53 (t, 2 H, OCH 2 ), (m, 12 H, CH(CH 3 ) 2 ) ppm. 31 P NMR (162 MHz, CDCl 3 ): δ = 149.4; ppm. Mass (m/z) for (M+Na) + : calcd ; found PhosTriPyr: 924 mg, 1.23 mmol, 99%, colourless oil. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.00 (s, 1 H, H5), 7.51 (m, 2 H, H5*, H3*), 7.41 (m, 2 H, DMT), (m, 7 H, DMT), 6.84 (m, 4 H, DMT), 6.56 (dd, 1 H, H4*), 6.25 (t, 1 H, H1 ), 5.44 (m, 2 H, CH 2 ), 4.54 (m, 2 H, H3, H4 ), 3.79 (m, 6 H, OCH 3 ), 3.59 (m, 2 H,CH(CH 3 ) 2 ), 3.46 (m, 2 H, CH 2 CN), 3.38 (m, 1 H, H5 or H5 ), 3.11 (m, 1 H, H5 or H5 ), 2.98 (m, 1 H, H2 or H2 ), 2.58 (m, 1 H, H2 or H2 ), 2.40 (t, 2 H, OCH 2 ), (m, 12 H, CH(CH 3 ) 2 ) ppm. 31 P NMR (162 MHz, CDCl 3 ): δ =148.9; ppm. Mass (m/z) for (M+Na) + : calcd ; found PhosTriPy: 459 mg, 0.58 mmol, 87%, colourless oil. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.55 (m, 1 H, H2*), 8.36 (s, 1 H, H5), 8.06 (dt, 1 H, H5*), 7.72 (td, 1 H, H4*), 7.38 (m, 2 H, DMT), (m, 8 H, DMT, H3*), 6.77 (m, 4 H, DMT), 6.40 (t, 1 H, H1 ), 4.74 (m, 1 H, H3 ), 4.31 (m, 1 H, H4 ), 3.72 (m, 6 H, OCH 3 ), (m, 4 H, CH(CH 3 ) 2, CH 2 CN), 3.29 (m, 2 H, H5, H5 ), 2.95 (m, 1 H, H2 or H2 ), 2.65 (m, 1 H, H2 or H2 ), 2.44 (t, 2 H, OCH 2 ), (m, 12 H, CH(CH 3 ) 2 ) ppm. 31 P NMR (162 MHz, CDCl 3 ): δ = 149.4; ppm. Mass (m/z) for (M+Na) + : calcd ; found
8 Characterization of the metal complexes [Cu(BnTriPyr) 2 ](NO 3 ) 2 2 CH 3 OH: 238 mg, 0.36 mmol, 74%, blue crystals. Metal salt used during synthesis: Cu(NO 3 ) 2 3 H 2 O No NMR spectra were recorded due to the paramagnetic behaviour of the complex. C 26 H 26 N 12 O 6 Cu (666.11): calcd. for [Cu(BnTriPyr) 2 ](NO 3 ) 2 : C 46.88, H 3.93, N 25.23; found C 46.84, H 3.80, N Mass (m/z) for {[Cu(BnTriPyr) 2 ](NO 3 )} + : calcd ; found [Pd(BnTriPyr) 2 ]Cl 2 2 H 2 O: 268 mg, yellow crystals. Metal precursor complex used during synthesis: [PdCl 2 (cod)] 1 H NMR (400 MHz, CDCl 3 ): δ = 8.51 (s, 1 H, H5p), 8.12 (s, 1 H, H5t), 7.88 (s, 1 H, H3p), 7.36 (m, 5 H, H2, H3, H4, H5, H6), 6.48 (s, 1 H, H4p), 5.78 (s, 2 H, H7), 5.71 (s, 2 H, H8) ppm. C 26 H 30 N 10 O 2 Cl 2 Pd (691.91): calcd. for [Pd(BnTriPyr) 2 ]Cl 2 2 H 2 O: C 45.13, H 4.37, N 20.24; found C 45.40, H 4.24, N Mass (m/z) for {[Pd(BnTriPyr) 2 ]Cl} + : calcd ; found
9 Molecular masses of the oligonucleotides as determined by mass spectrometry. Sequence Mass (calcd.) / Da Mass (found) / Da X/Y AGA-AAG-XGA-GGG-A Imi duplex I AGA-AAG-XGA-GGG-A TriTri duplex I AGA-AAG-XGA-GGG-A TriPyr duplex I AGA-AAG-XGA-GGG-A TriPy duplex I TCC-CTC-YCT-TTC-T Imi duplex I TCC-CTC-YCT-TTC-T TriTri duplex I TCC-CTC-YCT-TTC-T TriPyr duplex I TCC-CTC-YCT-TTC-T TriPy duplex I GAG-GGA-XAG-AAA-G Imi duplex II GAG-GGA-XAG-AAA-G TriTri duplex II GAG-GGA-XAG-AAA-G TriPyr duplex II GAG-GGA-XAG-AAA-G TriPy duplex II CTT-TCT-YTC-CCT-C Imi duplex II
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