Synthesis of glycosylated zinc (II) 5,15-diphenylporphyrin and zinc (II) 5,10,15,20-tetraphenylporphyrin analogs using Cu-catalyzed azide-alkyne 1,3-dipolar cycloaddition reactions

被引：19

作者：

Mukosera, George T. ^{[1
]}

Adams, Taylor P. ^{[2
]}

Rothbarth, Rachel F. ^{[2
]}

Langat, Hillary ^{[2
]}

Akanda, Shawon ^{[2
]}

Barkley, Rachel G. ^{[1
]}

Dolewski, Ryan D. ^{[3
]}

Ruppel, Joshua V. ^{[3
]}

Snyder, Nicole L. ^{[1
]}

机构：

[1] Davidson Coll, Dept Chem, Davidson, NC 28035 USA

[2] Hamilton Coll, Dept Chem, Clinton, NY 13323 USA

[3] SUNY Upstate Med Univ, Div Nat Sci & Engn, Spartanburg, SC 29303 USA

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 01期

关键词：

Carbohydrate; Click chemistry; Glycoporphyrin; Porphyrin; MANGANESE-GLYCOCONJUGATED PORPHYRINS; CLICK-CHEMISTRY; GLYCOPORPHYRIN DERIVATIVES; CARBOHYDRATE-RECOGNITION; MOLECULAR RECOGNITION; PHOTODYNAMIC THERAPY; AQUEOUS-MEDIA; EPOXIDATION; INHIBITION; DENDRIMERS;

D O I：

10.1016/j.tetlet.2014.10.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbohydrate porphyrin conjugates (CPCs) have gained attention for their ability to serve as water soluble catalysts and therapeutics for photodynamic therapy (PDT). However, the synthesis of these compounds continues to be a significant challenge. In this Letter we detail the direct synthesis of a series of glycosylated porphyrins prepared directly from Zn(II) 5,15-[p-(ethynyl)-diphenyl] or Zn(II) 5,10,15,20[p-(ethynyl)-diphenyl] porphyrins and per-O-acetylated sugar azides using copper catalyzed 1,3-dipolarcycloaddition reactions. The highest yields were achieved using a copper (II) catalyst reduced in situ, and we were able to achieve average yields greater than 90% per cycloaddition reaction. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：73 / 77

页数：5

共 3 条

[1] Synthesis of a new class of 5′-functionalized adenosines using a Rh(II)-catalyzed 1,3-dipolar cycloaddition
Liu, F
Austin, DJ
ORGANIC LETTERS, 2001, 3 (15) : 2273 - 2276
[2] Synthesis, crystal structures, and redox potentials of 2,3,12,13-tetrasubstituted 5,10,15,20-tetraphenylporphyrin zinc(II) complexes
Terazono, Y
Patrick, BO
Dolphin, DH
INORGANIC CHEMISTRY, 2002, 41 (25) : 6703 - 6710
[3] Layer-by-layer assembly of Zn(II) and Ni(II) 5,10,15,20-tetra(4-ethynylphenyl) porphyrin multilayers on Au using copper catalyzed azide-alkyne cycloaddition
Krawicz, Alexandra
Palazzo, Joseph
Wang, Gwo-Ching
Dinolfo, Peter H.
RSC ADVANCES, 2012, 2 (19) : 7513 - 7522

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