Mild Bioconjugation Through the Oxidative Coupling of ortho-Aminophenols and Anilines with Ferricyanide†
Allie C. Obermeyer
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorJohn B. Jarman
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorChawita Netirojjanakul
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorKareem El Muslemany
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthew B. Francis
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)Search for more papers by this authorAllie C. Obermeyer
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorJohn B. Jarman
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorChawita Netirojjanakul
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorKareem El Muslemany
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthew B. Francis
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460 (USA)Search for more papers by this authorThis work was supported by a grant from the NSF (CHE 1059083). A.C.O was supported by an NSF graduate research fellowship and the UC Berkeley Chemical Biology Program (NRSA Training Grant 1 T32 GMO66698). J.B.J. was supported by a SURF Rose-Hills summer research fellowship, and C.N. was supported by an HHMI International Student Fellowship.
Graphical Abstract
Having a complex: By using a small-molecule-based screen, ferricyanide was identified as an alternative, mild oxidant for the bioconjugation of anilines and o-aminophenols. The efficient coupling reaction is compatible with thiols and 1,2-diols, thus allowing its use in the creation of complex modified proteins.
Abstract
Using a small-molecule-based screen, ferricyanide was identified as a mild and efficient oxidant for the coupling of anilines and o-aminophenols on protein substrates. This reaction is compatible with thiols and 1,2-diols, allowing its use in the creation of complex bioconjugates for use in biotechnology and materials applications.
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