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

Y E Tsvetkov; A S Shashkov; Y A Knirel; U Zähringer

doi:10.1016/s0008-6215(01)00041-6

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

Carbohydr Res. 2001 Apr 12;331(3):233-7. doi: 10.1016/s0008-6215(01)00041-6.

Authors

Y E Tsvetkov¹, A S Shashkov, Y A Knirel, U Zähringer

Affiliation

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.

PMID: 11383892
DOI: 10.1016/s0008-6215(01)00041-6

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Legionella pneumophila / chemistry
Lipopolysaccharides / chemistry*
Nuclear Magnetic Resonance, Biomolecular
Optical Rotation
Sialic Acids / analysis*
Sialic Acids / chemical synthesis*

Substances

5,7-diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-glycero-talo-nonulosonic acid
Lipopolysaccharides
Sialic Acids
5,7-diacetamido-3,5,7,9-tetradeoxy-glycerogalacto-nonulosonic acid