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Synthesis of Glycoporphyrins

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Book cover Heterocycles from Carbohydrate Precursors

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

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.

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Authors and Affiliations

  1. Department of Chemistry, University of Aveiro, 3810-193, Aveiro, Portugal

    José A. S. Cavaleiro, João P. C. Tomé & Maria A. F. Faustino

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  1. José A. S. Cavaleiro
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  2. João P. C. Tomé
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  3. Maria A. F. Faustino
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Correspondence to José A. S. Cavaleiro .

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El Sayed H. El Ashry

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Cavaleiro, J.A.S., Tomé, J.P.C., Faustino, M.A.F. (2007). Synthesis of Glycoporphyrins. In: El Ashry, E.S.H. (eds) Heterocycles from Carbohydrate Precursors. Topics in Heterocyclic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_056

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