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The main carbohydrate ligand recognized by DC-SIGN is the high mannose glycan (Man)

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Abstract

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ABSTRACT

DC-SIGN is a novel DC-specific adhesion receptor on human Dentritic cells, which is essential in binding antigens and in transfecting the infection to T cells. DC-SIGN binds ligand motifs through a terminal carbohydrate recognition domain (CRD).

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The main carbohydrate ligand recognized by DC-SIGN is the high mannose glycan (Man)

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(GlcNAC)

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, a branched oligosaccharide presented in multiple copies by several pathogen glycoproteins. In the branched oligosaccharide, the terminal disaccharide portion Manα1-2Man binds DC-SIGN almost as efficiently as the entire high mannose glycan (Man)

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(GlcNAC). This suggest an important role of nonreducing end Manα1- 2Man fragment of Man

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in DC-SIGN recognition.

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Recently

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, it has been settled on a new class of DC-SIGN antagonists:

pseudodisaccharides in which the reducing mannose unit is replaced by a conformationally restricted dimethyl cycloexandicarboxylate.

The main purpose of this thesis project is to operate a stereoselective synthesis of new DC-SIGN antagonists, presenting a real D-carbamannose unit.

The crucial steps in the pathway towards the synthesis of the new pseudodisaccharides are: the transformation of the commercially available tri-O-acetyl-D-glucal (+)-2.1 into the 3,4-O-p-methoxybenzyl-D-glucal (-)-2.6 and theelaboration towards the pivotal 6- O-benzyl-β-epoxy-diol (+)-2.13, , precursor of the carbaglycosylating agents: the tri-O- benzyl (+)-2.16 and the tri-O-acetyl-β-epoxides (+)-2.22. The two carbaglycosylating agents were switched into the glycosyl acceptors (+)-2.17 and (+)-2.23, by a ring opening reaction with 2-azidoethanol.

Then, to build the pseudomannobiosides (+)-2.14 and (-)-2.15a, the carbamannose units

(+)-2.17 and (+)-2.23 are connected to an appropriate glycosyl donor, the

trichloroacetimidate (TCA) (-)-2.18 and the resulting pseudodisaccharides are subjected

to different steps of deprotection in order to obtain the desired pseudodisaccharides

fully-O-deprotected, with an ethoxy-amino and an ethoxy-azido functionality at the end.

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