Model O-glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate-containing calixarene derivatives named calixsugars. One or two sugar moieties (D-mannofuranose and D-glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]-arenes bearing two or four hydroxy-methyl groups at the upper rim were coupled with perbenzoylated thioethyl D-galactoside and D-lactoside in the presence of the thiophilic promoter copper(II) triflate. In this way β-linked bis and tetrakis-O-galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For the O-lactosyl derivatives only the bis-substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3-hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose-containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

Synthesis and properties of O-glycosyl calix[4]arenes (calixsugars)

DONDONI, Alessandro;MARRA, Alberto;
1997

Abstract

Model O-glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate-containing calixarene derivatives named calixsugars. One or two sugar moieties (D-mannofuranose and D-glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]-arenes bearing two or four hydroxy-methyl groups at the upper rim were coupled with perbenzoylated thioethyl D-galactoside and D-lactoside in the presence of the thiophilic promoter copper(II) triflate. In this way β-linked bis and tetrakis-O-galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For the O-lactosyl derivatives only the bis-substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3-hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose-containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.
1997
Dondoni, Alessandro; Marra, Alberto; Scherrmann, Mc; Casnati, A; Sansone, F; Ungaro, R.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1201451
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