Compact water-soluble bioconjugatable porphyrins

ORGN 475

K. Eszter Borbas, keborbas@ncsu.edu and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Dabney Hall, Raleigh, NC 27695
Diverse applications require access to water-soluble, bioconjugatable porphyrins. A symmetrically branched alkyl chain (“swallowtail”) bearing a charged group at each terminus imparts high water solubility (~20 mM) to a porphyrin upon attachment at one of the meso positions. The charged groups project above and below the plane of the porphyrin macrocycle. Here we present the synthesis of a water-soluble bioconjugatable porphyrin equipped with a bis-phosphonate swallowtail moiety and an iodoacetamide unit.