title: Synthesis of a fragment of bacterial cell wall.
abstract: Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the d-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the d-glucosamine as a building block.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
authors.forename: Dusan
authors.initials: D
authors.lastname: Hesek
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.forename: Ken-ichiro
authors.initials: K
authors.lastname: Morio
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D001419:Bacteria / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D009112:Muramic Acids / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010457:Peptidoglycan / Q000737:chemistry
chemical_list: C084900:(N-acetylmuramyl-N-acetylglucosaminyl)-alanyl-glutamyl-diaminopimelyl-alanine; D001685:Biological Factors; D004187:Disaccharides; D006027:Glycosides; D009112:Muramic Acids; D009842:Oligopeptides; D009844:Oligosaccharides; D010457:Peptidoglycan; C031651:N-acetylmuramic acid; D000117:Acetylglucosamine