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Ionization−Reactivity Relationships for Cysteine Thiols in Polypeptides†

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Department of Biology, University of Utah, Salt Lake City, Utah 84112-0840, and European Molecular Biology Laboratory, Meyerhofstrasse 1, D-69012, Heidelberg, Germany
Cite this: Biochemistry 1998, 37, 25, 8965–8972
Publication Date (Web):June 2, 1998
https://doi.org/10.1021/bi973101r
Copyright © 1998 American Chemical Society
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    Abstract

    Thiol−disulfide exchange reactions are required for many aspects of cellular metabolism including the folding of disulfide-bonded proteins, electron transfer, and numerous regulatory mechanisms. To identify factors influencing the rates of these reactions in polypeptides, the reactivities of Cys thiols in 16 model peptides were measured. For each of the peptides, which contained single Cys residues with thiol pKas ranging from 7.4 to 9.1, the rates of exchange with four disulfide-bonded compounds were measured. In reactions with two of the disulfide reagents, cystine and 2-hydroxyethyl disulfide, the peptide thiols displayed Brønsted correlations between reaction rate and pKa similar to those observed previously with model compounds (βnuc = 0.5 and 0.3, respectively). For two reagents with net charges, oxidized glutathione and cystamine, however, the apparent Brønsted coefficients were 0 and 0.8, respectively. These observations are in striking contrast with those obtained with model compounds, for which the Brønsted coefficients for the nucleophilic thiolates are largely independent of the disulfide-containing compound. The differences in the apparent Brønsted coefficients can be largely accounted for by electrostatic interactions between charged groups on the peptides and disulfide reagents and demonstrate that such interactions can play a dominant role in determining the rates of thiol−disulfide exchange in biological molecules. The results presented here provide an improved basis for predicting the rates of these reactions and suggest ways in which differences in the rates of competing reactions can be either minimized, to simplify the analysis of disulfide-coupled folding reactions, or enhanced, to favor formation of particular disulfides.

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    †

     Supported by Grant No. GM42494 from the U.S. National Institutes of Health.

    ‡

     University of Utah.

    §

     European Molecular Biology Laboratory.

    *

     Author to whom correspondence should be addressed. E-mail:  [email protected].

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