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Influence of Sulfoxide Group Placement on Polypeptide Conformational Stability

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    Influence of Sulfoxide Group Placement on Polypeptide Conformational Stability
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    • Eric G. Gharakhanian
      Eric G. Gharakhanian
      Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095, United States
      More by Eric G. Gharakhanian
    • Ehab Bahrun
      Ehab Bahrun
      Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095, United States
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    • Timothy J. Deming*
      Timothy J. Deming
      Department of Chemistry and Biochemistry  and  Department of Bioengineering, University of California Los Angeles, Los Angeles, California 90095, United States
      *[email protected]
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      Orcidhttp://orcid.org/0000-0002-0594-5025
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 37, 14530–14533
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    https://doi.org/10.1021/jacs.9b07223
    Published September 1, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    The synthesis of a homologous series containing five new nonionic sulfoxide containing polypeptides was described. Sulfoxide groups bestowed water solubility for all homologues, which allowed their use as a model for study of helix–coil transitions in water while avoiding contributions from charged groups or phase separation. Polypeptides were found to adopt chain conformations in water that were dependent on distance of sulfoxides from chain backbones, overall side-chain lengths, and solvent. These results allow preparation of polypeptide segments with different chain conformations without changing chemical functionality for potential use in structural studies and functional applications.

    Copyright © 2019 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b07223.

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    Cite this: J. Am. Chem. Soc. 2019, 141, 37, 14530–14533
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b07223
    Published September 1, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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