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

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

Volume: 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*

Affiliation:

• Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, P.O. Box 426, Alexandria 21321,Egypt

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

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.

Cite this article as:

Shehata A. Sahar , Narouz R. Mina , Soliman E. Sameh , Bassily W. Rafik , El-Sokkary I. Ramadan and Nashed A. Mina *, Regioselective Synthesis of Novel Galactose, Fucose and Lactose Fatty Acid Esters as Glycomimetics of Bile Acid 1-O-acyl Galactoside and Bacterial Glycolipids, Letters in Organic Chemistry 2018; 15 (2) . https://dx.doi.org/10.2174/1570178614666170720141917