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Issue 10, 2003
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Thiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties

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Abstract

The thiourea group has been exploited to link two or four carbohydrate units at the upper rim of tetrapropoxycalix[4]arene derivatives in the cone conformation. Two synthetic methodologies were used, the first one consisting of the condensation of di- and tetraminocalix[4]arenes with the isothiocyanate of monosaccharides in dry CH2Cl2 at room temperature and the second one exploiting the condensation of an aminolactoside with a calixarene isothiocyanate. The first method allows the glycoconjugates to be obtained in 75–80% overall yields. The difunctionalised derivatives exist in a closed flattened cone conformation in CDCl3 and CD3OD due to the formation of intramolecular hydrogen bonds involving the thiourea groups which are broken in DMSO-d6 to give an open flattened cone conformation. The thiourea groups act not only as linkers but also as binding units for anionic substrates as evidenced by solution 1H NMR and ESI-MS experiments. Turbidimetric analysis indicates that the tetraglucoside and tetragalactoside clusters give specific interactions with Concanavalin A (Con A) and peanut lectin (PNA), respectively. Both features show that the neoglycoconjugates could also be used as site specific molecular delivery systems.

Graphical abstract: Thiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties

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Publication details

The article was received on 12 Feb 2003, accepted on 26 Mar 2003 and first published on 08 Apr 2003


Article type: Paper
DOI: 10.1039/B301595E
Citation: Org. Biomol. Chem., 2003,1, 1802-1809
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    Thiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties

    F. Sansone, E. Chierici, A. Casnati and R. Ungaro, Org. Biomol. Chem., 2003, 1, 1802
    DOI: 10.1039/B301595E

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