Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction

René Roy, Sanjoy K. Das, Francisco Santoyo-González, Fernando Hernández-Mateo, Tarun K. Dam, C. Fred Brewer

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Abstract

A palladium-catalyzed Sonogashira reaction has been applied for the syntheses of divalent "sugar-rods" which exhibited excellent lectin cross-linking properties. The procedure, which involves a tetrakis(triphenylphosphine)-palladium-catalyzed cross-coupling reaction between an alkyne and a halogenbearing sp2-carbon in DMF at 60°C, is very efficient and the dimeric or heterobifunctional "sugar-rods" (8-13, 15-17) were isolated in 65-100% yields. Dimers 8 a and 15a were both shown to form insoluble cross-linked lattices when mixed with the tetrameric plant lectin from Canavalia ensiformis (Concavalin A, Con A). Moreover, the relative inhibitory properties of the synthetic dimannosides were determined by means of the hemagglutination of rabbit erythrocytes, whereby dimer 15a was shown to be 20-fold more potent than monomeric methyl α-D-mannopyranoside.

Original languageEnglish (US)
Pages (from-to)1757-1762
Number of pages6
JournalChemistry - A European Journal
Volume6
Issue number10
Publication statusPublished - May 15 2000

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Keywords

  • Alkenyls
  • Carbohydrates
  • Palladium
  • Sonogashira reaction
  • Sugar-rods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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