Synthesis of Biologically Active Sulfated and Phosphorylated Oligosaccharides

This review will highlight selected syntheses of biologically active charged carbohydrate structures and includes examples of glycosamino-glycans, i.e., heparin, and chondroitin 4 and 6 sulfates; selectin binding structures such as fucoidan repeating units, 3’-SO₃-Lewis^x and 3’-SO₃-Lewis^a; bacterial sulpholipids; phosphorylated high mannose structures, polyphosphorylated galactose compounds and inositol phosphates. Synthetic strategies and the methods utilized will be emphasized. The chemistry of carbohydrate structures having phosphodiester bonds between sugar moieties, i.e., nucleic acid synthesis, sugar nucleotide synthesis and the synthesis of glycosylphosphatidylinositide hydrolysis products will not be reviewed here due to the sheer volume of work in the respective areas. The biological activity of the compounds will only be discussed briefly in the introduction. The reader is encouraged to seek out the appropriate references for more in depth explanations of the biological significance of the targeted compounds.