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 Communications. 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.
synthesis, 5, 7-diamino-3, 7, Legionella pneumophila, 9-tetradeoxynon-2-ulosonic acid, identification of legionaminic acid, lipopolysaccharide components
NCBI PubMed ID: 11383892Publication DOI: 10.1016/S0008-6215(01)00041-6Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: uzaehr@fz-borstel.de
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, Forschungszentrum Borstel, Zentrum fur Medizin und Biowissenschaften, Parkallee 22, D- 23845 Borstel, Germany., Forschungszentrum Borstel, Zentrum fur Medizin und Biowissenschaften, Parkallee 22, D- 23845 Borstel, Germany