Synthesis of an orthogonally protected precursor to the glycan repeating unit of the bacterial cell wall.
[reaction: see text]. A synthesis of stereochemically pure and orthogonally protected N-acetyl-(2-deoxy-2-aminoglucopyranosyl)-beta-[1,4]-N-acetylmuramyl (NAG-NAM) monopeptide (2), the glycopeptide core of lipid II and of the bacterial cell wall repeating unit, is reported.
Saha
S L
SL
Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA.
Van Nieuwenhze
M S
MS
Hornback
W J
WJ
Aikins
J A
JA
Blaszczak
L C
LC
D001419:Bacteria / Q000737:chemistry*; D002473:Cell Wall / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D010457:Peptidoglycan / Q000737:chemistry*
C442272:11-epi-helioporin B; D004187:Disaccharides; D004224:Diterpenes; D007202:Indicators and Reagents; D010457:Peptidoglycan