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Regioselective Synthesis of Novel Galactose, Fucose and Lactose Fatty Acid Esters as Glycomimetics of Bile Acid 1-O-acyl Galactoside and Bacterial Glycolipids

[ Vol. 15 , Issue. 2 ]

Author(s):

Sahar A. Shehata, Mina R. Narouz, Sameh E. Soliman, Rafik W. Bassily, Ramadan I. El-Sokkary and Mina A. Nashed*   Pages 147 - 154 ( 8 )

Abstract:


Background: Carbohydrate fatty acid esters are found in important biological molecules such as bile acid 1-O-acyl galacto and bacterial glycolipids. The synthesis of glycomimetics of those biomolecules is required to study their structure-activity relationship.

Method: In this work a series of carbohydrate fatty acid esters were regioselectively prepared mainly via protection and deprotection and tin-mediated strategies of partially benzyl-protected sugars, followed by hydrogenolysis of the benzyl groups.

Results: We report here the regioselective synthesis of galactose palmitoyl esters along with other fatty acyl galactose glycomimetics namely fucose and lactose fatty esters. 1-O-palmitoyl-, 1,6-di-Opalmitoyl- D-galactose and 1-O-palmitoyl-L-fucose derivatives were prepared via a low-temperature esterification of the partially benzyl-protected galactose and fucose derivatives, respectively, followed by hydrogenolysis of the benzyl groups. The regioselective synthesis of 3'-O-acyl-D-lactosides of palmitic and nitrobenzoic acids was accomplished using a dibutyltin oxide activation strategy of partially protected lactoside derivatives.

Conclusion: The regioselective synthesis of galactose, fucose and lactose fatty acid esters as glycomimetics of biological molecules containing the 1-O-fatty acyl-D-galactose moiety is reported in this work.

Keywords:

Glycolipid, glycomimetics, sugar fatty acid esters, regioselective esterification, dibutyltin oxide, bile acid.

Affiliation:

Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321, Department of Chemistry, Faculty of Science, Damanhour University, Damanhour, Beheira, Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321, Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321, Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321, Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321

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