Determination of pK values for the bisulfite adducts of cytidine 5'-Monophosphate by carbon-13 nuclear magnetic resonance

Chow, N.H.; Triplett, J. W.; Smith, Stanford L.; Digenis, George A.

doi:10.1021/jo00411a040

Cited by 3 publications

(1 citation statement)

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“…The p K a values of 12 , 19 and 23 were determined by NMR titration. , We used 1 H NMR to determine the chemical shift of the side chain CH 2 of the Asp residue at different pH values. The Henderson−Hasselbach equation (eq 1) can also be written as where δ is the observed chemical shift in hertz for a resonance with a pH-dependent chemical shift (the Asp side chain CH 2 ) and δ max and δ min are the maximum and minimum observed chemical shifts, respectively, at the extremes of the pH range (2 to 7.5).…”

Section: Resultsmentioning

confidence: 99%

The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate

Joshi

Meier

1996

J. Am. Chem. Soc.

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A study of the effect of a helix dipole on the pK a of a side chain functional group has been undertaken to determine the magnitude of these electrostatic effects in the absence of interfering influences from a protein matrix. Three helical peptides were prepared: two containing Asp residues at the N- or C-terminus and one with an Asp residue in the middle of the peptide. These peptides have no reactive residues other than the Asp side chain carboxylate group. Circular dichroism confirmed that these peptides adopt helical conformations in aqueous solution over a broad pH range. The pK a of compound 12, where the Asp residue is at the N-terminus of the helix, is 3.81 ± 0.31. This is lower than the pK a of an Asp residue in a short nonhelical model compound (4.09 ± 0.21) and lower than the pK a values of 23, where the Asp residue is at the C-terminus of a helix (4.17 ± 0.24), and 19, where the Asp residue is in the middle of the helix (4.17 ± 0.29). No significant perturbation was observed at the C-terminus of a helix (compound 23), despite this being the negative pole of the dipole. We believe that this carboxylate is drawn toward the N-terminus by electrostatic attraction to the positive pole of the dipole, resulting in positioning of the carboxylate over the middle of the helix rather than over the C-terminus.

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Section: Resultsmentioning

confidence: 99%

The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate

Joshi

Meier

1996

J. Am. Chem. Soc.

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ChemInform Abstract: DETERMINATION OF PK VALUES FOR THE BISULFITE ADDUCTS OF CYTIDINE 5′‐MONOPHOSPHATE BY CARBON‐13 NUCLEAR MAGNETIC RESONANCE

Chow¹,

Triplett²,

Smith³

et al. 1978

Chemischer Informationsdienst

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The C6 configuration and syn/anti conformational preference of the bisulfite adducts of deoxyuridine and deoxycytidine by NMR and DFT calculations

Klika

Schüler

Miller

2014

Tetrahedron: Asymmetry

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Determination of pK values for the bisulfite adducts of cytidine 5'-Monophosphate by carbon-13 nuclear magnetic resonance

Cited by 3 publications

References 3 publications

The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate

The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate

ChemInform Abstract: DETERMINATION OF PK VALUES FOR THE BISULFITE ADDUCTS OF CYTIDINE 5′‐MONOPHOSPHATE BY CARBON‐13 NUCLEAR MAGNETIC RESONANCE

The C6 configuration and syn/anti conformational preference of the bisulfite adducts of deoxyuridine and deoxycytidine by NMR and DFT calculations

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Determination of pK values for the bisulfite adducts of cytidine 5'-Monophosphate by carbon-13 nuclear magnetic resonance

Cited by 3 publications

References 3 publications

The Effect of a Peptide Helix Macrodipole on the pKa of an Asp Side Chain Carboxylate

The Effect of a Peptide Helix Macrodipole on the pKa of an Asp Side Chain Carboxylate

ChemInform Abstract: DETERMINATION OF PK VALUES FOR THE BISULFITE ADDUCTS OF CYTIDINE 5′‐MONOPHOSPHATE BY CARBON‐13 NUCLEAR MAGNETIC RESONANCE

The C6 configuration and syn/anti conformational preference of the bisulfite adducts of deoxyuridine and deoxycytidine by NMR and DFT calculations

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Product

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The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate

The Effect of a Peptide Helix Macrodipole on the pK_a of an Asp Side Chain Carboxylate