Get access

Azobenzene Photoswitches for Staudinger–Bertozzi Ligation

Authors

  • Dr. Wiktor Szymański,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    Search for more papers by this author
  • Dr. Bian Wu,

    1. Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    Search for more papers by this author
  • Claudia Poloni,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    Search for more papers by this author
  • Prof. Dr. Dick B. Janssen,

    1. Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    Search for more papers by this author
  • Prof. Dr. Ben L. Feringa

    Corresponding author
    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    • Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    Search for more papers by this author

  • We thank P. van der Meulen for assistance with NMR measurements. We thank C. M. Jeronimus-Stratingh and A. van Dam for their assistance in acquiring the MS spectra. We thank Prof. B. W. Dijkstra from the University of Groningen for kindly providing the plasmid containing the LipA gene. Financial support from the NRSC-C catalysis, Royal Netherlands Academy of Sciences (KNAW academy chair), and European Research Council (ERC Advanced grant 227897) is gratefully acknowledged.

Abstract

original image

Click to switch: A novel family of azobenzenes containing residues needed for aqueous Staudinger–Bertozzi ligation to azides was designed (see scheme). The resulting photochromes show stable and reversible switching behavior in water, with a photostationary state (PSS) of up to 95:5 cis/trans. Applications in model systems include the modification of azide-bearing surfaces and proteins.

Ancillary