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J Biol Chem, Vol. 273, Issue 12, 7006-7017, March 20, 1998
1
2-Linked
D-glycero-D-manno-Heptopyranose
:K20)
From the Division of Medical and Biochemical Microbiology, Research
Center Borstel, Center for Medicine and Biosciences,
D-23845 Borstel, Germany
In a preliminary
investigation (Süsskind, M., Müller-Loennies, S., Nimmich,
W., Brade, H., and Holst, O. (1995) Carbohydr. Res. 269, C1-C7), we identified after deacylation of lipopolysaccharides (LPS)
from Klebsiella pneumoniae ssp. pneumoniae
rough strain R20 (O1:K20) as a major
fraction the
oligosaccharide,
where
Kdo was 3-deoxy-D-manno-oct-2-ulopyranosonic
acid and Hepp was manno-heptopyranose. The
presence of the threo-hex-4-enuronopyranosyl residue
indicated a substituent at O-4 of the second GalA residue linked to O-3
of the second L,D-Hep residue, which had been
eliminated by treatment with hot alkali. We now report the complete
structure of lipopolysaccharide, which was elucidated by additional
characterization of isolated core oligosaccharides and analysis of the
lipid A. The substituent at O-4 of the second GalpA is
D-GlcpN, which in a fraction of the LPS is
substituted at O-6 by three or four residues of
D-glycero-D-manno-heptopyranose
(D,D-Hepp). The complete
carbohydrate backbone of the LPS is as follows,
(L-glycero-D-manno-heptopyranose;
L,D-Hepp), where all hexoses
possess the D-configuration. Sugars marked with an asterisk are present in nonstoichiometric amounts. The structure is unique with
regard to the presence of an
1
2-linked
D-glycero-D-manno-heptoglycan (oligosaccharide), which has not been described to date, and does not
contain phosphate substituents in the core region. Fatty acid analysis
of lipid A identified (R)-3-hydroxytetradecanoic acid as
sole amide-linked fatty acid and (R)-3-hydroxytetradecanoic acid, tetradecanoic acid, small amounts of 2-hydroxytetradecanoic acid,
hexadecanoic acid, and traces of dodecanoic acid as ester-linked fatty
acids, substituting the carbohydrate backbone
D-GlcpN4P
16D-GlcpN1P. The nonreducing GlcN carries four fatty acids, present as two 3-O-tetradecanoyltetradecanoic acid residues, one of which
is amide-linked and the other ester-linked to O-3'. The reducing GlcN
is substituted in a nature fraction of lipid A by two residues of
(R)-3-hydroxytetradecanoic acid, one in amide and the other in ester linkage at O-3. Two minor fractions of lipid A were
identified; in one, the amide-linked
(R)-3-hydroxytetradecanoic acid at the reducing GlcN is
esterified with hexadecanoic acid, resulting in
3-O-hexadecanoyltetradecanoic acid, and in the second, one of the 3-O-tetradecanoyltetradecanoic acid residues at the
nonreducing GlcN is replaced by 3-O-dodecanoyltetradecanoic
acid. Thus, the complete structure of LPS is as shown in Fig.
1.
After immunization of BALB/c mice, two monoclonal antibodies were obtained that were shown to be specific for the core of LPS from K. pneumoniae ssp. pneumoniae, since they did not react with LPS or whole-cell lysates of a variety of other Gram-negative species. Both monoclonal antibodies could be inhibited by LPS but not by isolated oligosaccharides and are thus considered to recognize a conformational epitope in the core region.
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