Amino Acid Side Chain Induced Selectivity in the Hydrolysis of Peptides Catalyzed by a Zr(IV)-Substituted Wells-Dawson Type Polyoxometalate
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1 Amino Acid Side Chain Induced Selectivity in the Hydrolysis of Peptides Catalyzed by a Zr(IV)-Substituted Wells-Dawson Type Polyoxometalate Stef Vanhaecht, Gregory Absillis, Tatjana N. Parac-Vogt* Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium Supporting Information
2 Table S1. Fitting indices and hydrolysis yields at the end of the kinetic reaction. Dipeptide R 2 -value Hydrolysis yield Dipeptide R 2 -value Hydrolysis yield Gly-Gly 0, % Gly-Ser 0,99 97% Gly-Ala 0,999 73% Ser-Gly 0,986 50% Ala-Gly 0,982 73% Gly-Thr 0, % Gly-Val 0,993 69% Gly-Tyr 0,974 55% Gly-Leu 0,997 70% Leu-Ser 0, % Gly-Ile 0,993 94% Ile-Ser 0,966 75% Gly-Phe 0,996 96% Gly-Lys 0,996 75% Gly-Asp 0,994 95% Gly-Arg 0,996 81% Gly-Asn 0,972 92% Gly-His 0,991 94% Gly-Glu 0,997 56% His-Gly 0,995 81% Gly-Gln 0,986 77%
3 Conc. free Gly/Ala (mm) Electronic Supplementary Material (ESI) for Dalton Transactions 2,0 1,5 1,0 0,5 0, Time (min.) Figure S1. Concentration of the free amino acids Gly/Ala in function of time during the hydrolysis of 2mM Gly-Ala in the presence of 2mM of 1 (pd 5.0, 60 C). An exponential fit was used to determine the k obs of the hydrolysis reaction.
4 Table S2. Comparison of the reaction behavior of Gly-Ala and Ala-Gly in an equimolar mixture with 1(1:1, 2 mm, pd 5, 60 C). Dipeptide start- product t 1/2 for glycine formation Max.% of cyclic product Max.% of 'inversed' dipeptide Gly-Ala 30 days Ala-Gly 15.9 days 15 4
5 Table S3. Normalization factors for rate constant for the Gly-Aa dipeptides. (Factor = rate constant of the disappearance of the dipeptide / rate constant of growth free amino acid content) Dipeptide Normalization factor Gly-Gly 1.22 Gly-Ala 6.34 Gly-Val 1.0 Gly-Leu 4.58 Gly-Ile 1.29 Gly-Phe 1.58 Gly-Asp 1.99 Gly-Glu 2.94 Gly-Gln 3.87 Gly-Thr 1.26 Gly-Tyr 1.98 Gly-His 1.73
6 Table S4. Observed 13 C NMR chemical shift values for the dipeptide Gly-Asp both in the presence and absence of 1 at pd 5.0. Gly-Asp (ppm) Gly-Asp + Zr-WD-POM (ppm) (ppm) C O Asp (1) C O Gly (2) C O Asp (6) C Asp (3) C Gly (4) C Asp (5)
7 Table S5. Observed 13 C NMR chemical shift values for the dipeptide Gly-Glu both in the presence and absence of 1 at pd 5.0. Only the 1:2 species is found at these conditions 16 mm Gly- Glu (ppm) 16 mm Gly-Glu + 4 mm Zr-WD-POM (ppm) (ppm) Co Glu (1) Co Gly (2) Co Glu (7) Cα Glu (3) Cα Gly (4) Cβ Glu (5) Cγ Glu (6)
8 Table S6. Observed 13 C NMR chemical shift values for the dipeptide Gly-Glu both in the presence and absence of 1 at pd 5.0. About 83.1 % of 1:1 and 16.9 % of 1:2 species are present at these conditions. 2 mm Gly-Glu (ppm) 2 mm Gly-Glu mm Zr-WD-POM (ppm) (ppm) Co Glu (1) Co Gly (2) Co Glu (7) Cα Glu (3) Cα Gly (4) Cβ Glu (5) Cγ Glu (6)
9 Table S7. 1 H shifts of three protons in Gly-His at different pd-values. pd α-h Gly δ (ppm) C 7 -H δ (ppm) C 8 -H δ (ppm)
10 Figure S2. 1 H NMR spectrum of Gly-His in the presence (upper) and absence (lower) of 1 at different pd-values.
11 Figure S3. 13 C NMR spectrum of Gly-Arg in the presence (*) and absence of 1.
12 Table S8. Observed 13 C NMR chemical shift values for the dipeptide Gly-Arg both in the presence and absence of 1 at pd mm Gly- Arg 24.0 mm Gly-Arg mm 1 (ppm) C O Arg (1) C O Gly (2) C α Arg (3) C α Gly (4) C β Arg (5) C γ Arg (6) C δ Arg (7) C N Arg (8)
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