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Tetrahedron. 2008 Dec 8;64(50):11440-11448.

Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins.

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  • 1Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.


Three free base porphyrins have been prepared that bear a polar and facially encumbering 2,4,6-tris(carboxymethoxy)phenyl motif at one meso (5-) position. The only other substituent (15-position) comprises phenyl, formyl, or p-aminophenyl. The porphyrins exhibit solubility in water (or aqueous buffer solutions) at pH >/=7 and concentrations >1 mM at room temperature. The concise syntheses, water-solubility, and bioconjugatable handle make these porphyrin constructs suitable for biological applications.

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