Synthetic Studies on Sialoglycoconjugates 49: Novel Disaccharides and Lactams Composed of Sialic Acid and 1-Deoxynojirimycin-Potential for Biomedical Application

Abstract

Sialic acid-containing glycoconjugates participate in a variety of biological functions on cell surfaces, not only serving as receptors for hormones, viruses and bacteria but also as mediators in cell growth, differentiation, adhesion, oncogenesis and so on. For example, influenza virus^1,2 and tripanosoma cruzi ^3,4 recognize sialic acid in the time of infection to animal cells. Recently, the sialyl-Le^x (sLe^x) and sialyl-Le^a (sLe^a) carbohydrate epitopes have been highlighted as the ligands for selectins, a family of cell adhesion molecules involved in leukocyte traffic^5,6 and tumor metastasis.⁷ 1-Deoxynojirimycin (DNJ) and related compounds are well known⁸ as the potent inhibitors of a-glycosidases and glycoprotein-processing enzymes. Some of the Nsubstituted DNJ derivatives have been noted as antidiabetic and anti-HIV agents.