SUPPORTING INFORMATION. Recognition of Phosphopeptides by a Dinuclear Copper(II) Macrocyclic Complex in Water:Methanol 50:50 v/v Solution
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- Ευτρόπιος Βενιζέλος
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 SUPPORTING INFORMATION Recognition of Phosphopeptides by a Dinuclear Copper(II) Macrocyclic Complex in Water:Methanol 50:50 v/v Solution Lígia M. Mesquita, a Pedro Mateus, a Rui D. V. Fernandes, a Olga Iranzo, b Vânia André, c Filipe Tiago de Oliveira, d Carlos Platas-Iglesias, e Rita Delgado*,a a Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, Oeiras, Portugal. b Aix Marseille Univ., CNRS, Centrale Marseille, ism2, Marseille, France c Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, Portugal. d Laboratório de Instrumentação, Engenharia Biomédica e Física da Radiação (LIBPhys-UNL), Departamento de Física, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Monte de Caparica, Caparica, Portugal. e Centro de Investigaciones Científicas Avanzadas (CICA) and Departamento de Química Fundamental, Facultade de Ciencias, Universidade da Coruña, Campus da Zapateira-Rúa da Fraga 10, A Coruña, Spain. S1
2 Contents: Figures and Tables not shown in the main text Table S1 Overall protonation constants of L and overall stability constants of its copper(ii) S3 complexes Table S2 Overall and stepwise protonation constants of the studied substrates S3 Table S3 Overall stability constants of the copper(ii) complexes of the studied substrates S3 Table S4 Overall association constants between the copper(ii) complexes of L with the anions S4 Table S5 Hydrogen bond details for the main interactions in [Cu 2 L(μ-PhPO 4 )][Cu 2 L(μ- S4 PhPO 4 )(NO 3 )] 3NO 3 24H 2 O Table S6 Exchange coupling constants J iso (H = J iso S 1 S 2 ) calculated by DFT using different S5 functionals and basis sets for the cryptate reported in reference 24b. Table S7 Experimental (X-ray) and calculated (DFT) Bond Distances (Å) and Angles (º) of the S6 Coordination Spheres of the [Cu 2 L(μ-PhPO 4 )] 2+ (A) and [Cu 2 L(μ-PhPO 4 )(NO 3 )] + (B) Cation Complexes. Fig. S1 Species distribution diagram of the protonation of L S7 Fig. S2 Species distribution diagram of the protonation of H 2 pst3 S7 Fig. S3 Species distribution diagram calculated for the complexes of Cu 2+ with L in presence of S7 PhPO 2 4 anion Fig. S4 Thermal ellipsoid plot (at 50% probability) for the asymmetric unit, depicting all the S8 water molecules and anions Fig. S5 X-band EPR spectra of copper complexes (Cu 2+ :L 2:1) from ph 4.5 to 8.8 S8 Fig. S6 ESI mass spectrum of H 2 pst3 S9 Fig. S7 1 H NMR spectrum of H 2 pst3 in D 2 O S9 Fig. S8 APT NMR spectrum of H 2 pst3 in D 2 O S10 Fig. S9 1 H NMR spectrum of H 3 pst1 in D 2 O S10 Fig. S10 13 C NMR spectrum of H 3 pst1 in D 2 O S11 Fig. S11 COSY spectrum of H 3 pst1 in D 2 O S11 Fig. S12 HMQC spectrum of H 3 pst1 in D 2 O S12 Fig. S13 ESI mass spectrum of H 3 pst1 in H 2 O/MeOH S12 Fig. S14 1 H NMR spectrum of 2,4-bis(bromomethyl)-1,3,5-triethylbenzene in CDCl 3 S13 Fig. S15 1 H NMR spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S13 Fig. S16 13 C NMR spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S14 Fig. S17 COSY spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S14 Fig. S18 NOESY spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S15 Fig. S19 HMQC spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S16 Fig. S20 HMBC spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3 S16 Fig. S21 1 H NMR spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. S17 Fig. S22 13 C NMR spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3 S17 Fig. S23 COSY spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3 S18 Fig. S24 NOESY spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3 S18 Fig. S25 HMQC spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3 S19 Fig. S26 HMBC spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3 S19 Fig. S27 1 H NMR spectrum of L(imine) in CDCl 3. S20 Fig. S28 1 H NMR spectrum of L in CDCl 3. S20 Fig. S29 13 C NMR spectrum of L in CDCl 3 S21 Fig. S30 COSY spectrum of L in CDCl 3 S21 Fig. S31 NOESY spectrum of L in CDCl 3 S22 Fig. S32 HMQC spectrum of L in CDCl 3 S22 Fig. S33 HMBC spectrum of L in CDCl 3 S23 Fig. S34 ESI mass spectrum of L in H 2 O/MeOH S23 Fig. S35 ESI mass spectrum of the dicopper(ii) complex of L at ph = 6.5 in H 2 O/MeOH S24 Fig. S36 ESI mass spectrum of [Cu 2 L(μ-PhPO 4 )][Cu 2 L(μ-PhPO 4 )(NO 3 )]3NO 3 24H 2 O in MeOH S25 Fig. S37 UV-vis spectra of the dicopper complex of L at ph 7.0 and of this complex in presence S25 of PhPO 2 4 at ph 5.8 Table S8 Coordinates of the cryptate reported by Nelson (reference 24 in the main text) optimized S26 at the B3LYP/6-311G(d) level. Table S9 Coordinates of [Cu 2 L(µ-OH)] 3+ optimized at the B3LYP/6-311G(d) level. S28 Table S10 Coordinates of [Cu 2 L(µ- PhPO 4 )] 2+ optimized at the B3LYP/6-311G(d) level. S30 Table S11 Coordinates of [Cu 2 L(µ- PhPO 4 )(NO 3 )] + optimized at the B3LYP/6-311G(d) level. S33 Page S2
3 Table S1 Overall protonation constants (β i H ) of L and overall stability constants (β Cum H h L l ) of its copper(ii) complexes in water/methanol (50:50 v/v) solution. a Equilibrium reaction log β i H b Equilibrium reaction log Cum H h L l c L + H + HL (1) Cu H + + L [CuH 2 L] (1) L + 2 H + H 2 L (1) Cu 2+ + H + + L [CuHL] (2) L + 3 H + H 3 L (1) Cu 2+ + L [CuL] (3) L + 4 H + H 4 L (1) Cu 2+ + L [CuL(OH)] + + H (2) 2 Cu 2+ + L [Cu 2 L] (1) 2 Cu 2+ + L [Cu 2 L(OH)] 3+ + H (1) a T = K; I = M in KNO 3. b Values in parenthesis are standard deviations in the last significant figures. Table S2 Overall (β i H ) and stepwise (K i H ) protonation constants of the studied substrates in water/methanol (50:50 v/v) solution. a Equilibrium reaction b PO 4 3 H c log β i Equilibrium 2 PhPO reaction b 4 pst3 2 pst1 3 3 PO 4 PhPO 4 2 H log K i pst3 2 pst1 3 S + H + HS 11.91(1) 6.81(3) 10.69(1) 10.81(1) S + H + HS S + 2 H + H 2 S 19.42(1) (1) 17.35(3) HS + H + H 2 S S + 2 H + H 3 S 22.23(1) (1) 22.36(3) H 2 S + H + H 3 S a T = K; I = M in KNO 3. The value for acetate was also determined in the same conditions: log K 1 H = 5.24(1). b S denotes the substrate; charges of the substrates were omitted for simplicity. c Values in parenthesis are standard deviations in the last significant figures. Table S3 Overall (log β CuHh S s ) stability constants of the copper(ii) complexes of the studied substrates in water/methanol (50:50 v/v) solution. a Equilibrium reaction b,c PO 4 3 PhPO 4 2 d log β CuHh S s pst3 2 pst1 3 Cu H + + S [CuH 2 S] 23.89(5) 20.63(4) Cu 2+ + H + + S [CuHS] 16.76(2) 17.38(6) 16.04(1) Cu 2+ + S [CuS] 4.12(5) 11.11(3) a T = K; I = M in KNO 3. b S denotes the substrate. c Charges of the substrates and complexes were omitted for simplicity. d Values in parenthesis are standard deviations in the last significant figures. S3
4 Table S4 Overall (β Cu mhhllss ) association constants between the copper(ii) complexes of L with the anions in water/methanol (50:50 v/v). a Equilibrium reaction b,c PO 4 3 PhPO 4 2 d log β Cum H h L l S s pst3 2 pst1 3 2 Cu 2+ + L + S [Cu 2 L(S)] 25.84(1) 2 Cu 2+ + H + + L + S [Cu 2 HL(S)] 37.80(2) 36.57(1) 2 Cu H + + L + S [Cu 2 H 2 L(S)] 41.80(3) 45.38(1) 41.28(1) 2 Cu H + + L + S [Cu 2 H 3 L(S)] 48.89(7) 45.27(3) a T = ( ) K; I = ( ) M in KNO 3. b Charges of the complex species were omitted for simplicity. c S denotes the substrate. d Values in parenthesis are standard deviations in the last significant figures. Table S5 Hydrogen bond details for the main interactions in [Cu 2 L(μ-PhPO 4 )][Cu 2 L(μ- PhPO 4 )(NO 3 )]3NO 3 24H 2 O. Sym. Op. D H A d(h A) d(d A) (DĤA) (Å) (Å) ( ) x, y, z O15W O4A n/a 2.782(9) n/a x, y, z O16W O4A n/a 2.649(8) n/a -1+x, -1+y, z O11W O4B n/a 2.574(8) n/a -1+x, -1+y, z O17W O4B n/a 2.622(8) n/a x, y, z N1A H O16W (8) x, y, z N10A H O9W (10) x, 1+y, z N1B H O11W (8) 151 x, y, z N19B H O2C (10) 133 x, y, z N19B H O2D (10) 135 x, y, z N19A H O3C (10) 134 x, y, z N19A H O3D (10) 142 x, 1+y, z N10B H O (10) x, 1+y, z N28B H O17W (8) 153 x, y, z N28A H O4A (8) 138 x, y, z N28A H O15W (10) 144 S4
5 Table S6 Exchange coupling constants J iso (H = J iso S 1 S 2 ) calculated by DFT using different functionals and basis sets for the cryptate reported in reference 24b. J iso (cm -1 ) Cu-Cu (Å) Cu-O-Cu (º) M06/TZVP B3LYP/TZVP B3LYP/6-311G(d) a B3LYP/6-311G(d) b Exp a Structures optimized at the M06/TZVP level. b Structures optimized at the B3LYP/6-311G(d) level. S5
6 Table S7 Experimental (X-ray) and calculated (DFT) bond distances (Å) and angles (º) of the coordination spheres of the [Cu 2 L(μ-PhPO 4 )] 2+ and [Cu 2 L(μ-PhPO 4 )(NO 3 )] + cation complexes. [Cu 2 L(μ-PhPO 4 )] 2+ [Cu 2 L(μ-PhPO 4 )(NO 3 )] + X-ray M06/TZVP a B3LYP/6-311G(d) b X-ray B3LYP/6-311G(d) b Distances / Å N1 Cu (6) (7) N10 Cu (8) (5) N8 Cu (6) (6) O1 Cu (4) (6) O1C Cu (8) N19 Cu (6) (6) N26 Cu (6) (6) N28 Cu (6) (6) O3 Cu (6) (6) Cu1 Cu (1) (1) Angles / º N1 Cu1 N (2) (2) N8 Cu1 O (2) (3) O1C Cu2 N (3) O1C Cu2 N (3) 85.0 O1C Cu2 N (3) 84.1 O1C Cu2 O (3) 99.1 N19 Cu2 N (2) (2) N26 Cu2 O (2) (3) a Bulk solvent effects (water) included using polarized continuum model. b Optimizations in the gas phase. S6
7 Fig. S1 Species distribution diagram of the protonation of L. C L = M. Fig. S2 Species distribution diagram of the protonation of H 2 pst3. C peptide = M. Fig. S3 Species distribution diagram calculated for the complexes of Cu 2+ with L in presence of the PhPO 4 2 anion (A = PhPO 4 2 ). C Cu = 2 C L = 2 C A = M. S7
8 Fig. S4 Thermal ellipsoid plot (ellipsoids set at 50% probability) for the [Cu 2 L(μ-PhPO 4 )][Cu 2 L(μ-PhPO 4 )(NO 3 )]3NO 3 24H 2 O asymmetric unit, depicting all the water molecules and anions. Hydrogen atoms were omitted for clarity. Fig. S5 X-band EPR spectra of copper(ii) complexes (Cu 2+ :L 2:1) at three different ph values. All spectra recorded at 135 K, 2.0 mw microwave power, 1.0 mt modulation amplitude, and frequency (υ) of 9.5 GHz. All samples in H 2 O:MeOH (50:50 v/v) solution. S8
9 Fig. S6 ESI mass spectrum of H 2 pst3, recorded in positive ion mode. Fig. S7 1 H NMR spectrum of H 2 pst3 in D 2 O. S9
10 Fig. S8 APT NMR spectrum of H 2 pst3 in D 2 O. Fig. S9 1 H NMR spectrum of H 3 pst1 in D 2 O. S10
11 Fig. S10 13 C NMR spectrum of H 3 pst1 in D 2 O. Fig. S11 COSY spectrum of H 3 pst1 in D 2 O. S11
12 Fig. S12 HMQC spectrum of H 3 pst1 in D 2 O. Intens. x m/z Fig. S13 ESI mass spectrum of H 3 pst1 in H 2 O/MeOH, recorded in positive ion mode. S12
13 Fig. S14 1 H NMR spectrum of 2,4-bis(bromomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S15 1 H NMR spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. S13
14 Fig. S16 13 C NMR spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S17 COSY spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. S14
15 Fig. S18 NOESY spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. S15
16 Fig. S19 HMQC spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S20 HMBC spectrum of 2,4-bis(azidomethyl)-1,3,5-triethylbenzene in CDCl 3. S16
17 Fig. S21 1 H NMR spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S22 13 C NMR spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. S17
18 Fig. S23 COSY spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S24 NOESY spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. S18
19 Fig. S25 HMQC spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. Fig. S26 HMBC spectrum of 2,4-bis(aminomethyl)-1,3,5-triethylbenzene in CDCl 3. S19
20 Fig. S27 1 H NMR spectrum of L(imine) in CDCl 3. Fig. S28 1 H NMR spectrum of L in CDCl 3. S20
21 Fig. S29 13 C NMR spectrum of L in CDCl 3 Fig. S30 COSY spectrum of L in CDCl 3. S21
22 Fig. S31 NOESY spectrum of L in CDCl 3. Fig. S32 HMQC spectrum of L in CDCl 3. S22
23 Fig. S33 HMBC spectrum of L in CDCl 3 Fig. S34 ESI mass spectrum of L in H 2 O/MeOH, recorded in positive ion mode. S23
24 Intens. x m/z Intens. x10 6 Intens. x m/z m/z Fig. S35 ESI mass spectrum of a solution of the dicopper(ii) complex of L at ph = 6.5 in H 2 O/MeOH, and the zoom range of the isotopic series of peaks m/z 385 and 913, recorded in positive ion mode. S24
25 Intens. x10 7 Intens. x m/z m/z Fig. S36 ESI mass spectrum of crystals of [Cu 2 L(μ-PhPO 4 )][Cu 2 L(μ-PhPO 4 )(NO 3 )]3NO 3 24H 2 O dissolved in MeOH, and the zoom range of the isotopic series of peaks m/z 385 and 472, recorded in positive ion mode. Fig. S37 UV-vis spectra of the dicopper complex of L at ph 7.0 (left), and of this complex in presence of PhPO 4 2 at ph 5.8 and Cu 2+ :L:HPhPO 4 2:1:1 ratio (right). S25
26 Table S8 Coordinates of the cryptate reported by Nelson (reference 24 in the main text) optimized at the B3LYP/6-311G(d) level. Coordinates in Å Atom X Y Z Cu Cu O N N C C N C C C C C O C N C C C C N C C C C C O C N C C C C N C C C C C O C N S26
27 C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S27
28 H H H H H Table S9 Coordinates of [Cu 2 L(µ-OH)] 3+ optimized at the B3LYP/6-311G(d) level. Coordinates in Å Atom X Y Z Cu Cu N N N C C C C C C C N N C C C C C N C C C C C C C C C C C C C C C S28
29 C C C C C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S29
30 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Table S10 Coordinates of [Cu 2 L(µ-PhPO 4 )] 2+ optimized at the B3LYP/6-311G(d) level. Coordinates in Å Atom X Y Z Cu Cu P O N N N C C C C S30
31 C C C N N C C C C C N C C C C C C C C C C C C C C C C C C C C C C C C C C C C O O C C C C C S31
32 C C O C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S32
33 H H H H H H H H H H H H H H H H H H H H H Table S11 Coordinates of [Cu 2 L(µ-PhPO 4 )(NO 3 )] + optimized at the B3LYP/6-311G(d) level. Coordinates in Å Atom X Y Z Cu Cu P O N N N C C C C C C C N N C C S33
34 C C C N C C C C C C C C C C C C C C C C C C C C C C C C C C C C O O C C C C C C C O C H H H S34
35 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S35
36 H H H H H H H H H H H H H H O O O N S36
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