期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 38, 页码 6496-6503出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901128
关键词
Bacteriochlorin; Click chemistry; Cycloaddition; Glycoconjugates; Porphyrinoids
资金
- NIH through an AREA award [1R15GM119067-01]
- USC Upstate
- Office of Sponsored Awards and Research Support
- National Science Foundation [1624377]
- University of South Carolina
- Office of Undergraduate Research
- Beckman Foundation
- Boehringer Ingelheim Foundation
- HHU Stay Connected program
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1624377] Funding Source: National Science Foundation
Rapid and reproducible access to a series of unique porphyrin and bacteriochlorin glycoconjugates, including meso-glycosylated porphyrins and bacteriochlorins, and beta-glycosylated porphyrins, using 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 CuAAC glycosylation to porphyrins and bacteriochlorins based on the unique electronic properties of each ring system. Optimized 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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