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Titolo:
Synthesis of "sugar-rods" with phytohemagglutinin cross-linking propertiesby using the palladium-catalyzed Sonogashira reaction
Autore:
Roy, R; Das, SK; Santoyo-Gonzalez, F; Hernandez-Mateo, F; Dam, TK; Brewer, CF;
Indirizzi:
Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada Univ Ottawa Ottawa ON Canada K1N 6N5 ept Chem, Ottawa, ON K1N 6N5, Canada Yeshiva Univ Albert Einstein Coll Med, Dept Mol Pharmacol & Microbiol & Immunol, Bronx, NY 10461 USA Yeshiva Univ Albert Einstein Coll Med Bronx NY USA 10461 nx, NY 10461 USA
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 10, volume: 6, anno: 2000,
pagine: 1757 - 1762
SICI:
0947-6539(20000515)6:10<1757:SO"WPC>2.0.ZU;2-4
Fonte:
ISI
Lingua:
ENG
Soggetto:
CONCANAVALIN-A; METATHESIS REACTION; DYNEMICIN-A; PEA LECTINS; BINDING; CHEMISTRY; GLYCOSIDES; DENDRIMERS; ENEDIYNES; HALIDES;
Keywords:
alkenyls; carbohydrates; palladium; Sonogashira reaction; sugar-rods;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Roy, R Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada Univ Ottawa Ottawa ON Canada K1N 6N5 m, Ottawa, ON K1N 6N5, Canada
Citazione:
R. Roy et al., "Synthesis of "sugar-rods" with phytohemagglutinin cross-linking propertiesby using the palladium-catalyzed Sonogashira reaction", CHEM-EUR J, 6(10), 2000, pp. 1757-1762

Abstract

A palladium-catalyzed Sonogashira reaction has been applied for the syntheses of divalent "sugar-rods" which exhibited excellent lectin cross-linkingproperties, The procedure, which involves a tetrakis(triphenylphosphine)palladium-catalyzed cross-coupling reaction between an alkyne and a halogen-bearing sp(2)-carbon in DMF at 60 degrees C, is very efficient and the dimeric or hetero-bifunctional "sugar-rods" (8-13, 1517j were isolated in 65-100% yields. Dimers 8a 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 alpha-D-mannopyranoside.

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Documento generato il 03/07/20 alle ore 01:38:33