Abstract
The structure of the lipid A component of Rhodopseudomonas gelatinosa 29/1 lipopolysaccharide was established. It constitutes a β-1,6-glucosamine disaccharide substituted on either side by ester-and glycosidically-bound phosphate residues. Both phosphate groups are in turn nonstoichiometrically substituted by ethanolamine. The amino groups of the disaccharide are N-acylated by 3-acyloxyacyl residues: that at the reducing glucosamine by 3-O-(14:0) 10:0, and that at the non-reducing one by 3-O-(12:0)10:0. Hydroxyl groups at C-3 and C-3′ are esterified by hydroxycapric acid. Hydroxyl groups at C-4 and C-6′ in free hydroxycapric acid. Hydroxyl groups at C-4 and C-6′ in free lipid A were shown to be unoccupied by methylation with diazomethane. A similar methylation of the intact lipopolysaccharide revealed a free hydroxyl group only at C-4, indicating that C-6′ is the attachment site of 3-deoxy-d-anno-octulosonic acid.
By preparative thin-layer chromatography free lipid A could be resolved into at least two major and one minor fractions. Lipid A of R. gelatinosa 29/1 shows high lethal toxicity, comparable to that of Salmonella lipid A.
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Abbreviations
- GlcN:
-
d-Glucosamine
- dOclA:
-
2-keto-3-deoxy-d-manno-octonate
- GC-MS:
-
combined gas liquid chromatographymass spectrometry
- LPS:
-
lipopolysaccharide
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Dedicated to Prof. Dr. Gerhart Drews on the occasion of his 60th birthday
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Tharanathan, R.N., Salimath, P.V., Weckesser, J. et al. The structure of lipid A from the lipopolysaccharide of Rhodopseudomonas gelatinosa 29/1. Arch. Microbiol. 141, 279–283 (1985). https://doi.org/10.1007/BF00428837
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DOI: https://doi.org/10.1007/BF00428837