Synthesis of Porphyrin and Bacteriochlorin Glycoconjugates through CuAAC Reaction Tuning

被引：22

作者：

Bennion, Matthew C. ^{[1
]}

Burch, Morgan A. ^{[2
]}

Dennis, David G. ^{[1
]}

Lech, Melissa E. ^{[1
]}

Neuhaus, Kira ^{[2
,3
]}

Fendler, Nikole L. ^{[2
]}

Parris, Matthew R. ^{[1
]}

Cuadra, Jessica E. ^{[1
]}

Dixon, Charlie F. ^{[1
]}

Mukosera, George T. ^{[2
]}

Blauch, David N. ^{[2
]}

Hartmann, Laura ^{[3
]}

Snyder, Nicole L. ^{[2
]}

Ruppel, Joshua, V ^{[1
]}

机构：

[1] Univ South Carolina Upstate, Div Nat Sci & Engn, 800 Univ Way, Spartanburg, SC 29303 USA

[2] Davidson Coll, Dept Chem, 102 North Main St, Davidson, NC 28035 USA

[3] Heinrich Heine Univ Dusseldorf, Inst Organ Chem & Macromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 38期

基金：

美国国家科学基金会;

关键词：

Bacteriochlorin; Click chemistry; Cycloaddition; Glycoconjugates; Porphyrinoids; 1,3-DIPOLAR CYCLOADDITION; CLICK-CHEMISTRY; GLYCOPORPHYRIN DERIVATIVES; PHOTODYNAMIC THERAPY; D-GALACTOSE; GLYCOCLUSTERS; EPOXIDATION; CHLORINS; SUGAR; ACID;

D O I：

10.1002/ejoc.201901128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6496 / 6503

页数：8

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