Heterocycles from Carbohydrate Precursors pp 179-248

Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 7)

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Synthesis of Glycoporphyrins

  • José A. S. Cavaleiro
  • João P. C. Tomé
  • Maria A. F. Faustino
Chapter

Abstract

Porphyrins and carbohydrates are two groups of natural compounds that are vital to our life. However, only a few examples of glycoporphyrins have been isolated from a natural source. The attachment of saccharide units to porphyrin macrocycles gives rise to derivatives which might be of great significance for certain medicinal and other applications. Synthetic methodologies published during the last 20 years leading to such glycoporphyrin derivatives have been reviewed. Glycoporphyrin derivatives can be obtained by chemical transformation of natural porphyrins or by synthesis from adequate precursors. Such precursors can be porphyrins adequately substituted for the glycoderivatization to take place or can be pyrrolic and glycoaldehyde species, which give rise to target glycoporphyrins by acid catalyzed condensations. Glycochlorins, another group of derivatives of great biological significance, have been synthesized in recent years. The recently reported 1,3-dipolar cycloaddition reactions of porphyrins with glyconitrones and glyco-azomethine ylides have provided a new avenue for the synthesis of such compounds.

Carbohydrates Glycochlorins Glycoporphyrins PDT Porphyrins  

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Copyright information

© Springer-Verlag Berlin Heidelberg 2007

Authors and Affiliations

  • José A. S. Cavaleiro
    • 1
  • João P. C. Tomé
    • 1
  • Maria A. F. Faustino
    • 1
  1. 1.Department of ChemistryUniversity of AveiroAveiroPortugal

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