The conjugation of carbohydrates to porphyrins has gained attention due to increased solubility in polar solvents, leading to enhanced pharmacological uptake; making them a viable option for medicinal applications. Previous strategies for CPCs synthesis included classical condensation of glycosyl aldehydes with pyrrole or pyrrole derivatives; or the substitution of amino and hydroxyl-substituted porphyrins with functionalized sugars. However, these strategies typically face difficult challenges including, lengthy synthesis of starting materials and challenging purification of the conjugated product. The use of “click chemistry”, specifically Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), has provided a modular approach and mild conditions for the synthesis of carbohydrate porphyrin conjugates from easily synthesized starting materials. We have demonstrated the direct conjugation of carbohydrates onto the meso, beta, and aryl positions of the porphyrin macrocycle. Our current focus is the creation of CPCs functionalized on the meso position with a C-O cross-coupled alkyl chain linker terminated with an alkyne moiety. A library of CPCs with a variety of carbohydrates and linkers will provide an opportunity to explore the relationship between proximity of the carbohydrate and the observed biological activity.

Cu(I)-catalyzed azide-alkyne cycloaddition synthesis of carbohydrate porphyrin conjugates

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.