Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis.
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
Nikolaev
Andrei V
AV
College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK. a.v.nikolaev@dundee.ac.uk
Botvinko
Irina V
IV
Ross
Andrew J
AJ
D000818:Animals; D001419:Bacteria / Q000737:chemistry; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry; D006031:Glycosylation; D007891:Leishmania / Q000737:chemistry; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry; D010755:Organophosphates / Q000138:chemical synthesis / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D015003:Yeasts / Q000737:chemistry
D019081:O Antigens; D010755:Organophosphates; D011134:Polysaccharides