Supplementary Data. Department of Biochemistry and Molecular Biology, Department of Chemistry, and Michael Smith
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1 Supplementary Data ph-dependent random coil 1 H, 13 C, and 15 N chemical shifts of the ionizable amino acids: a guide for protein pk a measurements Gerald Platzer #, Mark Okon 2, and Lawrence P. McIntosh * Department of Biochemistry and Molecular Biology, Department of Chemistry, and Michael Smith Laboratories, University of British Columbia, Vancouver BC, V6T 1Z3, Canada # Present address: Department of Structural and Computational Biology, Max F. Perutz Laboratories, University of Vienna, Vienna Biocenter Campus 5, A-1030 Vienna, Austria *Corresponding author: Lawrence P. McIntosh Department of Biochemistry and Molecular Biology Life Sciences Centre, 2350 Health Sciences Mall University of British Columbia Vancouver, B.C. Canada, V6T 1Z3 Phone: (001) mcintosh@chem.ubc.ca 1
2 Table S1 ph-dependent chemical shifts (ppm) of the ionizable amino acids in blocked Ac-Gly-X-Gly-NH 2 tripeptides a Δ calc. N-terminal amine: Alanine- (pk a 8.23) Ala 1 H H (amine) 8.04 Hα Hβ (methyl) C Cα Cβ (methyl) CO N N (amine) H H 2 N (Z) 7.24 H 2 N (E) N N C-terminal carboxylic acid: N- alanine (pk a 3.55) 1 H CH 3 (methyl) C CH 3 (methyl) CO Ala 1 H HN Hα Hβ (methyl) C Cα Cβ (methyl) CO N N
3 Δ calc. Aspartic acid: Ac-Gly-Asp-Gly-NH 2 (pk a 3.86) 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN Hα (avg.) C Cα CO N N Asp 1 H HN Hα Hβ (avg.) H2 (carboxyl) > C Cα Cβ Cγ (carboxyl) CO N N Gly(+1) 1 H HN Hα (avg.) C Cα CO N N H H 2 N (Z) H 2 N (E) N N
4 Δ calc. Glutamic acid: Ac-Gly-Glu-Gly-NH 2 (pk a 4.34) 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN Hα (avg.) C Cα CO N N Glu 1 H HN Hα Hβ (avg.) Hγ Hε2 (carboxyl) > C Cα Cβ Cγ C (carboxyl) CO N N Gly(+1) 1 H HN Hα (avg.) C Cα 44.9 CO N N H H 2 N (Z) H 2 N (E) N N
5 Δ calc. Histidine: Ac-Gly-His-Gly-NH 2 (pk a 6.45) c 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN Hα (avg.) C Cα CO N N b His c 1 H HN 8.55 ~8.35 d ~ Hα ~ 4.75 d 4.59 ~ Hβ (avg.) H Hε H1 >10 Hε2 >10 13 C Cα Cβ Cγ C Cε CO N N b N b Nε b Gly(+1) 1 H HN 8.55 Hα (avg.) C Cα CO N N b H H 2 N (Z) H 2 N (E) N N
6 Δ calc. Cysteine: Ac-Gly-Cys-Gly-NH 2 (pk a 8.49) 1 H CH 3 (methyl) C CH 3 (methyl) C CO H HN 8.32 Hα (avg.) C Cα CO N N b Cys 1 H HN 8.48 Hα Hβ (avg.) Hγ (thiol) ~ 2.0 e 13 C Cα Cβ CO N N b Gly(+1) 1 H HN 8.58 Hα (avg.) C Cα CO N N b H H 2 N (Z) H 2 N (E) N N
7 Δ calc. Tyrosine: Ac-Gly-Tyr-Gly-NH 2 (pk a 9.76) 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN 8.21 Hα (avg.) C Cα CO N N b Tyr 1 H HN 8.16 Hα Hβ (avg.) H Hε Hη (phenol) ~ 9.3 e 13 C Cα Cβ Cγ C Cε Cζ CO N N b Gly(+1) 1 H HN 8.44 Hα (avg.) C Cα CO 15 N N H H 2 N (Z) 7.07 H 2 N (E) N N
8 Δ calc. Lysine: Ac-Gly-Lys-Gly-NH 2 (pk a 10.34) 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN 8.31 Hα (avg.) C Cα CO N N b Lys 1 H HN 8.40 Hα Hβ (avg.) Hγ H Hε Hζ (amine) 7.52 ~ 1-2 f ~ - 6 f C Cα Cβ Cγ C Cε CO N N b Nζ (amine) 32.7 ~ 25.2 g ~ g H HN 8.50 Hα (avg.) C Cα CO N N b H H 2 N (Z) 7.07 H 2 N (E) N N
9 Δ calc. Arginine: Ac-Gly-Arg-Gly-NH 2 (pk a ~ 13.9) 1 H CH 3 (methyl) C CH 3 (methyl) CO H HN Hα (avg.) C Cα CO N N Arg 1 H HN Hα Hβ (avg.) Hγ H 3.21 ~ 3.04 ~ Hε (guan.) Hη (guan.) C Cα Cβ Cγ C Cζ (guan.) ~ ~ CO N N Nε (guan.) Nη (guan.) ~ 71 h ~ 71 h 1 H HN Hα (avg.) C Cα CO N N H H 2 N (Z) H 2 N (E) N N
10 a Recorded at 25 o C with 50 mm NaCl and 5% D 2 O, unless indicated. Reported are the fit pk a values and end point chemical shifts (ppm) of the of the acid and conjugate base forms, along with the chemical shift change upon deprotonation (Δ; negative is upfield) and the predicted shift at ph 7. The estimated errors are ± 0.05 for pk a values (± 0.1 for arginine), ± 0.02 ppm for 1 H nuclei, ± 0.08 ppm for 13 C, and ± 0.06 ppm for 15 N. Blank values indicate not determined. Prochiral proton shifts are averaged. The C-terminal protons are assigned assuming Z/E as upfield/downfield. b Recorded in 99% D 2 O and corrected for the deuterium isotope shift. c Data for neutral histidine is an average of ~80% N ε2 H and ~20% N 1 H tautomers. d Estimated from (Kjaergaard et al. 2011). e From the BioMagResBank (Ulrich et al. 2008). f From (Takayama et al. 2008). g From (Andre et al. 2007). h From 13 C 6 / 15 N 4 -L-arginine (Table S2). 10
11 Table S2 ph-dependent chemical shifts (ppm) of 13 C 6 / 15 N 4 -L-arginine a,b (HAH) ph ~ 7 ph ~ 11.5 ph > 15 Δ due to amine (HA - HAH) Δ due to guan. α-cooα-nh 3 + guan+ α-cooα-nh 2 guan+ α-cooα-nh 2 guan 1 H HN (amine) 7.81 Hα Hβ (avg.) < Hγ < H Hε 7.22 Hη C Cα Cβ Cγ C Cζ CO N N (amine) Nε Nη a Recorded at 25 o C for 100 mm 13 C 6 / 15 N 4 -L-arginine with 5% D 2 O, 1 mm DSS, and initially 50 mm NaCl (final KOH > 10 M). Blank values indicate not determined due to rapid HX or spectral overlap. The 1 H β shifts are averaged. Due to bond rotations, the two 15 N η and four 1 H η yield broad signals. The data for neutral arginine are tautomer averaged. b Tabulated are the fit chemical shifts for the two-step sequential titration from ph 7 to of the α-aminium (pk a 9.15 ± 0.05) and then the guanidinium (pk a 13.9 ± 0.1) moieties in the context of the α-carboxylate anion. The estimated fitting errors are ± 0.05 ppm for 1 H nuclei, ± 0.1 ppm for 13 C, ± 0.15 ppm for 15 N amine and 15 N ε, and ± 0.3 ppm for 15 N η. 11
12 Supplemental References Andre I, Linse S, Mulder FAA (2007) Residue-specific pk(a) determination of lysine and arginine side chains by indirect 15 N and 13 C NMR spectroscopy: Application to apo calmodulin. J Am Chem Soc 129: Kjaergaard M, Brander S, Poulsen FM (2011) Random coil chemical shift for intrinsically disordered proteins: effects of temperature and ph. J Biomol NMR 49: Takayama Y, Castaneda CA, Chimenti M, Garcia-Moreno B, Iwahara J (2008) Direct evidence for deprotonation of a lysine side chain buried in the hydrophobic core of a protein. J Am Chem Soc 130: Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M. Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF. Tolmie DE, Wenger RK, Yao HY, Markley JL (2008) BioMagResBank. Nucleic Acids Res 36:D402-D408 12
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