2,4-DIHYDROXYPENTANOIC ACIDS: NEW NON-SUGAR COMPONENTS OF BACTERIAL POLYSACCHARIDES

Alexander S. Shashkov, Nina A. Kocharova, Filip V. Toukach, Vadim V. Kachala, Yuriy A. Knirel

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

KEYWORDS: Providencia alcalifaciens; 2,4-dihydroxypentanoic acid; sugar ether; bacterial polysaccharide structure

Natural Product Communications, 2008, v. 3(10), pp. 1625-1630

New components of bacterial polysaccharides, (2S,4R)- and (2R,4R)-2,4-dihydroxypentanoic acids, were identified using two-dimensional ¹H and ¹³C NMR spectroscopy in the O-antigens of Providencia alcalifaciens O8 and O31. The acids were ether-linked via their 2-HO-group to a residue of N-acetylglucosamine or mannose at position 4. The absolute configurations of the acids were determined by NOE spectroscopy combined with molecular modeling.

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