Stereocontrolled Synthesis of Sialosides

Department of Chemistry, Wayne State University, Detroit, MI, USA 

Glycochemical Synthesis Strategies and Applications, First Edition. 

Edited by Shang-Cheng Hung and Medel Manuel L. Zulueta. 

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Cell-surface sialic acid residues play important roles in diverse biological processes [86]. Sialic acids are usually found in terminal positions linked through an a-glyco-sidic linkage. The stereoselective synthesis of a-sialosides remains a challenge because the glycosides have the thermodynamically unfavorable equatorial orientation and the anomeric carbon is a very hindered quaternary center [4]. Enzymatic sialylation is, therefore, an attractive alternative means of preparation of a-sialosides in an efficient and stereocontrolled manner. 

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