Entropic contribution of elongation factor P to proline. positioning at the catalytic center of the ribosome
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1 S1 Supplementary Data for Entropic contribution of elongation factor P to proline positioning at the catalytic center of the ribosome Lili K. Doerfel, Ingo Wohlgemuth, Vladimir Kubyshkin, Agata L. Starosta, Daniel N. Wilson, Nediljko Budisa, and Marina V. Rodnina Figure S1: Functional characterization of Pro*-tRNA Pro. (a) Aminoacylation of trna Pro obtained from cells (closed circles) and by T7 RNA-polymerase transcription (open circles) with [ 14 C]Pro by purified Pro-RS. (b) fmppg with native trna Pro (open symbols) and trna Pro transcript (closed symbols) in the absence (circles) or presence of EF-P (triangles). (c) Isolation of the TC by SEC. The upper panel shows purification of [ 14 C]Pro-tRNA Pro ternary complex (with EF-Tu and GTP). The middle peak corresponds to the TC, as shown by radioactively labeled aa-trna. The first peak corresponds to Pro-RS (the dashed profile was obtained with purified aa-trna) and the third peak contains uncharged trna and EF-Tu. The lower panels show the profile for TCs with X-tRNA Pro with X= 4,4-F -Pro, 4-R-Hyp and 4-S-Flp as representatives for Pro analogs. The ratio trna/ef-tu is kept constant, such that the TC-forming efficiency can be estimated from the ratio of peak/peak3.
2 S Figure S: Arrhenius plots of fmp*-pmn formation with and without EF-P. The Pmn reaction with fmet-s-flp-trna Pro (triangles) and fmet-r-flp-trna Pro (circles), without EF- P (open symbols) or with EF-P (closed symbols). Shown are average values and SD from up to four replicates. Because the rate of the Pmn reaction with fmet-r-flp-trna Pro in the presence of EF-P at 37 C was too rapid for the quench-flow apparatus, the value could not be determined with precision and was therefore excluded from the fitting.
3 S3 Table S1: Equilibrium and kinetic parameters of amide rotation for Pro and analogs. Pro* -ΔG a tc, kcal/mol Ref. -ΔG b tc, kcal/mol Ref. k ct (Pro*)/ k ct (Pro) Ref. Pro 0.90 ± 0.03 c ± 0.0 = 1 - Aze 0.8 ± 0.04 d d,e (19 e,f ) 3 Pip 1.13 ± 0.05 d d,e (54 e,f ) 3 4-S-Flp 0.54 ± 0.0 c ± c,e 4-R-Flp 1.13 ± 0.04 c ± c,e 4,4-F -Pro 0.76 ± 0.03 c ± c,e 4-S-Hyp g 0.49 ± 0.0 c 0.54 ± c,e 4-R-Hyp 1.07 ± 0.04 c ± c,e (1.1 e,h ) 5 ( 6 ) cis-mepro g 1.04 ± 0.04 c e,i (0.9 e,f ) j trans-mepro g 1.40 ± 0.05 c e,i (16 e,f ) j 4-S-Mep 1.19 ± 0.04 c h,k 7 4-R-Mep 0.77 ± 0.03 c h,k 7 3,4-Dhp g 1.00 ± 0.03 c 0.98 ± c,e (.1 h,k ) ( 8 ) Ala 3.04 ± 0.05 l Phe 3.03 ± 0.01 l Val 3.4 ± 0.11 l Values were determined in Ac-Pro*-X; a calculated as ΔG = -RTlnK for 98 K; b calculated as ΔG = ΔH TΔS; c X = OCH 3 ; d X = 4-nitroanilide; e experimental value; f X = O - ; g values determined in this work; h X = NHCH 3 ; i within Ac-GG-Pro*-GG-NH peptides; j to be published elsewhere; k theoretical value; l X = OH Ac-4-S-Hyp-OCH 3 1 H NMR (D O, 700 MHz): 4.73 (dd, J = 7.4, 3. Hz, 1H, α-ch, cis), 4.56 (dd, J = 9.6,.6 Hz, 1H, α-ch, trans), 4.47 (m, 1H, γ-ch, trans), 4.43 (m, 1H, γ-ch, cis), 3.74 (dd, J = 11.7, 4.5 Hz, 1H, δ-ch1, trans), 3.71 (s, 3H, CH3O, cis), 3.67 (s, 3H, CH3O, trans), 3.54 (dd, J = 1.8, 4.3 Hz, 1H, δ-ch1, cis), 3.51 (dm, J = 11.7 Hz, 1H, δ-ch, trans), 3.38 (dm, J = 1.8 Hz, 1H, δ-ch, cis), (m, H, cis: β-ch, 1H, trans: β-ch1),.1 (dm, J = 13.8 Hz, 1H, β- CH, trans),.05 (s, 3H, CH3C=O, trans), 1.99 (s, 3H, CH3C=O, cis). Ac-cis-MePro-OCH 3 1 H NMR (D O, 600 MHz), only trans-conformer: 4.75 (m, 1H, α-ch), 3.64 (s, 3H, CH3O), 3.50 (dt, J = 6.,.7 Hz, δ-ch),.61 (td, J = 1.9, 6. Hz, β-ch1),.17 (s, 3H, CH3C=O), 1.99 (dd, J = 1.9, 3.7 Hz, 1H, β-ch), 1.71 (m, 1H, γ-ch), 0.84 and 0.71 (two m, H, CH). Ac-trans-MePro-OCH 3 1 H NMR (D O, 600 MHz), only trans-conformer: 4.7 (dd, J = 9.7, 5.4 Hz, 1H, α-ch), 3.67 (s, 3H, CH3O), 3.47 (ddd, J = 6.6, 5.7,.4 Hz, 1H, δ-ch),.33 (ddd, J = 13.7, 9.5, 1.3 Hz, β-ch1),.1 (m, 1H, β-ch),.16 (s, 3H, CH3C=O), 1.78 (m, 1H, γ-ch), 0.93 (dt, J = 8.7, 5.8 Hz, 1H, CH1), 0.58 (td, J = 5.5,.5 Hz, 1H, CH). Ac-3,4-Dhp-OCH 3 1 H NMR (D O, 700 MHz): 6.04 (dm, J = 6 Hz, 1H, γ-ch, trans+cis), 5.8 (dm, J = 6 Hz, 1H, β-ch, cis), 5.78 (dm, J = 6 Hz, 1H, β-ch, trans), 5.33 (m, 1H, α-ch, cis), 5.09 (m, 1H, α-ch, trans), 4.38 (dm, J = 15. Hz, δ-ch1, trans), 4.34 (dm, J = 15. Hz, 1H, δ-ch, trans), 3.74 (s, 3H, CH3O, cis), 3.69 (s, 3H, CH3O, trans),.07 (s, 3H, CH3C=O, trans), 1.94 (s, 3H, CH3C=O, cis).
4 S4 Table S: The pk a values. amino acid pk a, amino group a pk a, carboxyl group b pk a s-trans s-cis Weight Average c Pro Aze Pip S-Flp R-Flp ,4-F -Pro S-Hyp R-Hyp cis-mepro trans-mepro S-Mep R-Mep ,4-Dhp Ala Phe Val a values for the free amino acids determined in aqueous buffer at 98 K 10 ; For comparison, previously reported amino-group pk a values for Pro, 4-R-Flp, 4,4-F -Pro, and 4-R-Hyp, are 10.8, 9., 7., and 9.7, respectively 5 ; b pk a values of the carboxyl-group of Ac-Pro* are taken from 9. c The weight average pk a was calculated from the cis and trans pk a s taken the cis-trans equilibrium into account (Table S1).
5 S5 Table S3: Rate of reactions for Pro and Pro-derivatives Pro* k hydrol k aminol fmp*-pmn fmp*g fmp*p*g no EF-P no EF-P no EF-P 10-5 s s -1 k pep, s -1 k pep, s -1 k obs, s -1 k obs, s -1 k obs, s -1 k obs, s -1 Pro 6.3 ± ± ± ± ± ± ± ± 0.0 Aze 0.55 ± 0.6 (40%) 0.1 ± 0.04 (60%) 45 ± 13 (34%).4 ± 0.3 (66%) Pip 0.5 ± 0.06 (68%) 0.03 ± 0.01(3%) 7 ± 3 (81%) 0.7 ±0. 3 (19%) 4-S-Flp 3 ± 0.3 ± ± ± ± ± 0.5 no product ± R-Flp 3 ± 1 9 ± 3 1 ± 11 ± ± ± 9 0. ± ± ,4-F -Pro 31 ± 1 8 ± 5.3 ± ± 5 4 ± 4 (73%) 65 ± 14 (83%) ± ± ± 0.0 (7%) 0.3 ± 0.3 (17%) 4-S-Hyp 14 ± 1 4 ± ± ± ± ± ± ± R-Hyp 6.3 ± ± 0. ± ± ± ± ± ± 0.04 Cis-MePro 1.7 ± ± ± ± ± ± no product ± 0.00 Trans-MePro 8.4 ± ± ± ± 8 ± 4 (68%) 69 ± 11 (86%) ± ± ± 0.5 (3%) 0.6 ± 0.5 (14%) 4-S-Mep 3.7 ± ± 0.00 (1%) 6 ± 1(38%) 9 ± 4 (3%) 6 ± 9 (7%) ± ± ± (79%) 0.18 ± 0.03 (6%) 0.16 ± 0.03 (68%) 1 ± 1 (8%) 4-R-Mep 3.8 ± ± ± ± 1 19 ± 3 (69%) 73 ± 9 (75%) 0.07 ± ± ± 0. (31%) 1.9 ± 0.6 (5%) 3,4-Dhp 5.6 ± ± ± ± ± 0.4 (67%) 1 ± 4 (8%) ± ± ± 0.07 (33%) 0. ± 0.1 (18%) fmet 11 ± ± 1
6 S6 Table S4: Activation parameters of the Pmn reaction with fmet-r/s-flp-trna Pro for 37 C Pro*, EF-P G, kcal/mol H, kcal/mol T S, kcal/mol 4-R-Flp, no EF-P 16 ± 1 ± 6.4 ± R-Flp, EF-P 15 ± 1 4 ± ± S-Flp, no EF-P ± 1 19 ± -.3 ± 0. 4-S-Flp, EF-P 19 ± 1 4 ± ± 0.3 Calculated for 37 C, H = E a -RT, G = H -T S, T S (37 C)= T S (5 C)*310.15K/98.15K References (1) Shoulders, M. D.; Raines, R. T. Annu. Rev. Biochem. 009, 78, 99. () Renner, C.; Alefelder, S.; Bae, J. H.; Budisa, N.; Huber, R.; Moroder, L. Angew. Chem., Int. Ed. 001, 40, 93. (3) Kern, D.; Schutkowski, M.; Drakenberg, T. J. Am. Chem. Soc. 1997, 119, (4) Shoulders, M. D.; Kamer, K. J.; Raines, R. T. Bioorg. Med. Chem. Lett. 009, 19, (5) Eberhardt, E. S.; Panisik, N., Jr.; Raines, R. T. J. Am. Chem. Soc. 1996, 118, 161. (6) Owens, N. W.; Braun, C.; O'Neil, J. D.; Marat, K.; Schweizer, F. J. Am. Chem. Soc. 007, 19, (7) Kang, Y. K.; Byun, B. J.; Park, H. S. Biopolymers 011, 95, 51. (8) Kang, Y. K.; Park, H. S. Biopolymers 009, 9, 387. (9) Kubyshkin, V.; Durkin, P.; Budisa, N. submitted for publication. (10) Kubyshkin, V.; Afonin, S.; Kara, S.; Budisa, N.; Mykhailiuk, P. K.; Ulrich, A. S. Org Biomol Chem 015, 13, 3171.
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