Synthesis of β-Cyclodextrin, Per-O-glycosylated through an Ethylene Glycol Spacer Arm

Africa García-Barrientos; Juan J. García-López; Joaquín Isac-García; Fernando Ortega-Caballero; Clara Uriel; Antonio Vargas-Berenguel; Francisco Santoyo-González

doi:10.1055/s-2001-14574

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Synthesis of β-Cyclodextrin, Per-O-glycosylated through an Ethylene Glycol Spacer Arm

Africa García-Barrientos^a, Juan J. García-López^b, Joaquín Isac-García^a, Fernando Ortega-Caballero^b, Clara Uriel^a, Antonio Vargas-Berenguel*^b, Francisco Santoyo-González*^a
^a Instituto de Biotecnología, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
^b Área de Química Orgánica, Universidad de Almería, 04120 Almería, Spain
Fax: +34-958243186; +34-950015481; e-Mail: fsantoyo@ugr.es; avargas@ual.es;

Abstract

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Abstract

The synthesis of cyclodextrin-based O-α-manno, O-β-galactopyranoside and O-β-galactofuranoside clusters, having seven sugar residues attached to the core, through ethylene, ethylenoxyethylene and ethylene-(dioxyethylene)-ethylene spacer arms is described. The synthesis involves the glycosylation of the oxyethylene arm and the attachment of the O-glycosides onto the heptakis(6-deoxy-6-iodo)-β-cyclodextrin derivative by means of nucleophilic displacement reaction using cesium carbonate in dimethylformamide.

Key words

carbohydrates - cyclodextrins - glycosylation - macrocycles - oligosaccharides

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