Synthesis and identification in bacterial lipopolysaccharides of 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids.
5,7-Diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids were synthesized by condensation of 2,4-diacetamido-2,4,6-trideoxy-D-mannose with oxalacetic acid. Comparison of the 1H and 13C NMR data and the specific optical rotation values of these monosaccharides and the corresponding L-glycero-D-galacto and L-glycero-D-talo isomers synthesized earlier [Tsvetkov, Y. E.; Shashkov, A. S.; Knirel, Y. A.; Backinowsky, L. V.; Zähringer, U. Mendeleev Commun. 2000, 90-92] with data of the natural compounds enabled the identification in bacterial lipopolysaccharides of derivatives of 5,7-diamino-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic (legionaminic) acid and epimers of legionaminic acid at C-4 and C-8.
Tsvetkov
Y E
YE
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
Shashkov
A S
AS
Knirel
Y A
YA
Zähringer
U
U
D016952:Legionella pneumophila / Q000737:chemistry; D008070:Lipopolysaccharides / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D012794:Sialic Acids / Q000032:analysis* / Q000138:chemical synthesis*
C110570:5,7-diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-glycero-talo-nonulosonic acid; D008070:Lipopolysaccharides; D012794:Sialic Acids; C050215:5,7-diacetamido-3,5,7,9-tetradeoxy-glycerogalacto-nonulosonic acid