In:
European Journal of Organic Chemistry, Wiley, Vol. 2019, No. 38 ( 2019-10-17), p. 6496-6503
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2019.38
DOI:
10.1002/ejoc.201901128
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
1475010-7
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