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Updated: May 13, 2026

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
Published on: July 6, 2012
Rational synthesis and characterization of a novel pH-responsive pyranoflavylium-starch conjugate from potato
Mariana Cunha1, Ana Sofia Pires1, Ivo E Sampaio-Dias1
1REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua Do Campo Alegre, 687, 4169-007, Porto, Portugal.
Abstract:
A pH-responsive 4'-hydroxy-10-aminoethylcarbamoylpyranoflavylium dye (PyFlav) inspired by natural compounds was synthesized and conjugated to chemically functionalized starch derived from potato industry sidestreams. The PyFlav dye was characterized through LC-DAD/ESI-MS, 1D and 2D NMR, and UV-VIS spectroscopy, with acidic constant values determined as pKa1 = 5.19 ± 0.03; pKa2 = 9.27 ± 0.22. Potato-derived native starch was oxidized and then covalently bound to the amine-containing PyFlav dye, yielding a starch-PyFlav conjugate through a Schiff base reaction. The structural and chemical properties of the oxidized starch and starch-PyFlav conjugate were studied by FTIR-ATR spectroscopy, which confirmed successful functionalization by the emergence of an imine bond in the conjugate. This conjugation will permit the formation of pH-responsive membranes/films to exploit their application as smart colorimetric labels for food spoilage monitoring.
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