Oxidative Modification of Tryptophan-Containing Peptides

Jonas Petersen, Katrine E. Christensen, Mathias T. Nielsen, Kim T. Mortensen, Vitaly V. Komnatnyy, Thomas Eiland Nielsen, Katrine Qvortrup

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    Abstract

    We herein present a broadly useful method for the chemoselective modification of a wide range of tryptophan-containing peptides. Exposing a tryptophan-containing peptide to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a selective cyclodehydration between the peptide backbone and the indole side chain of tryptophan to form a fully conjugated indolyl-oxazole moiety. The modified peptides show a characteristic and significant emission maximum at 425 nm, thus making the method a useful strategy for fluorescence labeling.
    Original languageDanish
    JournalACS Combinatorial Science
    Volume20
    Issue number6
    Pages (from-to)344-349
    Number of pages6
    ISSN2156-8952
    DOIs
    Publication statusPublished - 2018

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