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    Oxime Catalysis by Freezing
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    Department of Biochemistry, Cardiovascular Research Institute Maastricht (CARIM), University Maastricht, Maastricht 6229 ER, The Netherlands
    *E-mail: [email protected]
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2016, 27, 1, 42–46
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    https://doi.org/10.1021/acs.bioconjchem.5b00611
    Published December 9, 2015
    Copyright © 2015 American Chemical Society
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    Abstract

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    Chemical reaction rates are generally decreased at lower temperatures. Here, we report that an oxime ligation reaction in water at neutral pH is accelerated by freezing. The freezing method and its rate effect on oxime ligation are systematically studied on a peptide model system, and applied to a larger chemokine protein, containing a single acetyl butyrate group, which is conjugated to an aminooxy-labeled ligand. Our improved ligation protocol now makes it possible to efficiently introduce oxime-bond coupled ligands into proteins under aqueous conditions at low concentrations and neutral pH.

    Copyright © 2015 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.bioconjchem.5b00611.

    • Experimental methods and a supplemental figure showing the effect of methanol on oxime ligation (PDF)

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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2016, 27, 1, 42–46
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.bioconjchem.5b00611
    Published December 9, 2015
    Copyright © 2015 American Chemical Society
    Request reuse permissions

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