An azide-alkyne 1,3-dipolar cycloaddition reaction (“click” reaction) was employed to create a library of porphyrin and bacteriochlorin glycoconjugates.  These aromatic macrocycles have potential applications as photosensitizers in photodynamic therapy, the study of protein interactions, among other applications.  A series of azido mono- and di-saccharides were gylcoconjugated to alkynylated bacteriochlorins in addition to the meso- and beta- positions of alkynylated-porphyrins utilizing the 1,3-dipolar cycloaddtion “click” reaction.  These reactions were carried out under mild conditions under acidic (porphyrin) and basic (bacteriochlorin) protocols.  Porphyrin glycoconjugations were obtained in high yields with the beta-alkynylated porphyrin generating almost quantitative yields with both mono- and di-saccharides.  In addition, we found that switching the protocol to basic conditions while still utilizing the 1,3-dipolar cycloaddition reaction greatly improved the yield and reproducibility of the bacteriochlorin glycoconjugation reaction.

Synthesis of porphyrin- and bacteriochlorin-based glycoconjugates using an azide-alkyne 1,3 dipolar cycloaddition reaction

2019 Spring National Meeting

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