Synthesis of a fragment of bacterial cell wall.
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.
Hesek
Dusan
D
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Lee
Mijoon
M
Morio
Ken-ichiro
K
Mobashery
Shahriar
S
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
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