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, Curtis F. Brewer

Research output: Contribution to journalArticle

47 Citations (Scopus)

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
StatePublished - May 15 2000

Fingerprint

Palladium
Phytohemagglutinins
Sugars
Dimers
Plant Lectins
Alkynes
Lectins
Carbon
methylmannoside
triphenylphosphine

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction. / Roy, René; Das, Sanjoy K.; Santoyo-González, Francisco; Hernández-Mateo, Fernando; Dam, Tarun K.; Brewer, Curtis F.

In: Chemistry - A European Journal, Vol. 6, No. 10, 15.05.2000, p. 1757-1762.

Research output: Contribution to journalArticle

Roy, René ; Das, Sanjoy K. ; Santoyo-González, Francisco ; Hernández-Mateo, Fernando ; Dam, Tarun K. ; Brewer, Curtis F. / Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction. In: Chemistry - A European Journal. 2000 ; Vol. 6, No. 10. pp. 1757-1762.
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AU - Dam, Tarun K.

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