ArticleThe FEBS journal2012
Influence of peptide dipoles and hydrogen bonds on reactive cysteine pKa values in fission yeast DJ-1.
Article in The FEBS journal, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
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- Changes in an Enzyme Ensemble During Catalysis Observed by High Resolution XFEL Crystallography.bioRxiv : the preprint server for biology · 2023Article
- Aurora Kinase A Regulation by Cysteine Oxidative Modification.Antioxidants (Basel, Switzerland) · 2023Review
- Understanding Cysteine Chemistry Using Conventional and Serial X-Ray Protein Crystallography.Crystals · 2022Article
- Profiling the Site of Protein CoAlation and Coenzyme A Stabilization Interactions.Antioxidants (Basel, Switzerland) · 2022Article
- Phosphorylated cofilin-2 is more prone to oxidative modifications on Cys39 and favors amyloid fibril formation.Redox biology · 2020Article
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- Weak Acid-Base Interactions of Histidine and Cysteine Affect the Charge States, Tertiary Structure, and Zn(II)-Binding of Heptapeptides.Journal of the American Society for Mass Spectrometry · 2019Article
- Redox Signaling by Reactive Electrophiles and Oxidants.Chemical reviews · 2018Review
- L718Q mutant EGFR escapes covalent inhibition by stabilizing a non-reactive conformation of the lung cancer drug osimertinib.Chemical science · 2018Article
- Protein palmitoylation: Palmitoyltransferases and their specificity.Experimental biology and medicine (Maywood, N.J.) · 2017Article
- Short Carboxylic Acid-Carboxylate Hydrogen Bonds Can Have Fully Localized Protons.Biochemistry · 2017Article
- Novel Redox-Dependent Esterase Activity (EC 3.1.1.2) for DJ-1: Implications for Parkinson's Disease.International journal of molecular sciences · 2016Article
- Structural Basis for Redox Regulation of Cytoplasmic and Chloroplastic Triosephosphate Isomerases fromFrontiers in plant science · 2016Article
- A Two-step Protein Quality Control Pathway for a Misfolded DJ-1 Variant in Fission Yeast.The Journal of biological chemistry · 2015Article
- Identification of glutathione (GSH)-independent glyoxalase III from Schizosaccharomyces pombe.BMC evolutionary biology · 2014Article
- A glutathione-independent glyoxalase of the DJ-1 superfamily plays an important role in managing metabolically generated methylglyoxal in Candida albicans.The Journal of biological chemistry · 2014Article
- Mechanism of the modulation of BK potassium channel complexes with different auxiliary subunit compositions by the omega-3 fatty acid DHA.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
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3 authors.
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Abstract
Cysteine residues with depressed pK(a) values are critical for the functions of many proteins. Several types of interactions can stabilize cysteine thiolate anions, including hydrogen bonds between thiol(ate)s and nearby residues as well as electrostatic interactions involving charged residues or dipoles. Dipolar stabilization of thiolates by peptide groups has been suggested to play a particularly important role near the N-termini of α-helices. Using a combination of X-ray crystallography, site-directed mutagenesis and spectroscopic methods, we show that the reactive cysteine residue (Cys111) in Schizosaccharomyces pombe DJ-1 experiences a 0.6 unit depression of its thiol pK(a) as a consequence of a hydrogen bond donated by a threonine side chain (Thr114) to a nearby peptide carbonyl oxygen at the N-terminus of an α-helix. This extended hydrogen bonded interaction is consistent with a sum of dipoles model whereby the distal hydrogen bond polarizes and strengthens the direct hydrogen bond between the proximal amide hydrogen and the cysteine thiol(ate). Therefore, our results suggest that the local dipolar enhancement of hydrogen bonds can appreciably stabilize cysteine thiolate formation. However, the substitution of a valine residue with a proline at the i + 3 position has only a minor effect (0.3 units) on the pK(a) of Cys111. As proline has a reduced peptide dipole moment, this small effect suggests that a more extended helix macrodipolar effect does not play a major role in this system.
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