ArticleEuropean journal of organic chemistry2019
Synthesis of Porphyrin and Bacteriochlorin Glycoconjugates through CuAAC Reaction Tuning.
Article in European journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Pursuing the Red-Shift in GlycoporphyrinsA New Synthetic Approach toward Glycoconjugates from theACS organic & inorganic Au · 2026Article
- High-performance Fe-Al@BTC MOF for supercapacitor and antibacterial applications: experimental, DFT, and molecular docking studies.Scientific reports · 2026Article
- Targeted photodynamic therapy for breast cancer: the potential of glyconanoparticles.Nanoscale advances · 2023Article
- Dipyrrinato-Iridium(III) Complexes for Application in Photodynamic Therapy and Antimicrobial Photodynamic Inactivation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis and evaluation of porphyrin glycoconjugates varying in linker length: preliminary effects on the photodynamic inactivation ofRSC advances · 2021Article
- Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1-Azides, Porphyrins and Corroles.Molecules (Basel, Switzerland) · 2020Review
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Authors and funding
14 authors.
Funding
Abstract
Rapid and reproducible access to a series of unique porphyrin and bacteriochlorin glycoconjugates, including meso-glycosylated porphyrins and bacteriochlorins, and beta-glycosylated porphyrins, via copper catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) is reported for the first time. The work presented highlights the system-dependent reaction conditions required for glycosylation to porphyrins and bacteriochlorins based on the unique electronic properties of each ring system. Attenuated reaction conditions were used to synthesize fifteen new glycosylated porphyrin and bacteriochlorin analogs in 74 - 99% yield, and were extended to solid support to produce the first oligo(amidoamine)-based porphyrin glycoconjugate. These compounds hold significant potential as next generation water soluble catalysts and photodynamic therapy/photodynamic inactivation (PDT/PDI) agents.
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