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
References
Böchner BR, Maron DM, Ames BN (1981) Detection of phosphate esters on chromatograms: an improved reagent. Anal Biochem 17:81–83
Caroff M, Szabo L (1983) Identification of 2-amino-6-O-(2-amino-2-deoxy-β-d-glucopyranosyl)-2-deoxy-d-glucose as a major constituent of the hydrophobic region of the Bordetella pertussis endotoxin. Carbohydr Res 114:95–102
Galanos C, Roppel J, Weckesser J, Rietschel E.Th, Mayer H (1977) Biological activities of lipopolysaccharides and lipid A from Rhodospirillaceae. Infect Immun 16:407–412
Hase S, Rietschel ETh (1976a) Isolation and analysis of the lipid A backbone. Lipid A structure of lipopolysaccharides from various bacterial groups. Eur J Biochem 63:101–107
Hase S, Rietschel ETh (1976b) Methylation analysis of glucosaminitol and glucosaminyl-glucosaminitol disaccharides. Formation of 2-deoxy-2-(N-acetyl-acetamido)-glucitol derivatives. Eur J Biochem 63:93–99
Holst O, Borowiak D, Weckesser J, Mayer H (1983) Structural studies on the phosphate-free lipid A of Rhodomicrobium vannielii ATCC 17100. Eur J Biochem 137:325–332
Lüderitz O, Freudenberg MA, Galanos C, Lehmann V, Rietschel ETh, Shaw DH (1982) Lipopolysaccharides of gram-negative bacteria. In: Razin S, Rottem S (eds) Current topics in membrane transport, vol 17. Academic Press, New York, pp 79–151
Mayer H, Weckesser J (1984) Unusual lipid A's: structures, taxonomical relevance and potential value for endotoxin research. In: Rietschel ETh (ed) Chemistry of endotoxin. Elsevier North Holland, Amsterdam, pp 221–247
Mayer H, Salimath PV, Holst O, Weckesser J (1984) Unusual lipid A types in phototrophic bacteria and related species. Rev Infect Dis 6:542–545
Ohno K, Nishiyama H, Nagase H (1979) A mild methylation of alcohols with diazomethane catalyzed by silica gel. Tetrahedron Lett 45:4405–4406
Rietschel ETh, Wollenweber HW, Brade H, Zähringer U, Lindner B, Seydel U, Bradaczek H, Barnickel G, Labischinsky H, Giesbrecht P (1984) Structure and conformation of the lipid A component of lipopolysaccharides. In: Rietschel ETh (ed) Chemistry of endotoxin. Elsevier-North-Holland, Amsterdam, pp 187–220
Salimath PV, Weckesser J, Strittmatter W, Mayer H (1983) Structural studies on a non-toxic lipid A from Rhodopseudomonas sphaeroides ATCC 17023. Eur J Biochem 136:195–200
Salimath PV, Tharanathan RN, Weckesser J, Mayer H (1984) The structure of the polysaccharide moiety of Rhodopseudomonas sphaeroides ATCC 17023 lipopolysaccharide. Eur J Biochem 144:227–232
Stevenson AFG, Mönig H, Weckesser J (1981) Radioprotective and haemopoietic effects of some lipopolysaccharides from Rhodospirillaceae species in mice. Experientia 37:1331–1332
Tharanathan RN, Weckesser J, Mayer H (1978) Structural studies on the d-arabinose-containing lipid A from Rhodospirillum tenue 2761. Eur J Biochem 84:385–394
Weckesser J, Mayer H, Drews G, Fromme I (1975) Lipophilic O-antigens containing d-glycero-d-mannoheptose as sole neutral sugar in Rhodopseudomonas gelatinosa. J Bacteriol 123:449–455
Weckesser J, Drews G, Mayer H (1979) Lipopolysaccharides of photosynthetic prokaryotes. Ann Rev Microbiol 33:215–239
Wollenweber HW, Rietschel ETh (1985) Analysis of lipopolysaccharide (lipid A) fatty acids. Methods Carbohydr Chem 9 (in press)
Wollenweber HW, Broady K, Lüderitz O, Rietschel ETh (1982a) The chemical structure of lipid A: demonstration of amide-linked 3-acyloxyacyl-residues in Salmonella minnesota Re lipopolysaccharide. Eur J Biochem 124:191–198
Wollenweber HW, Schlecht S, Lüderitz O, Rietschel ETh (1982b) Fatty acid in lipopolysaccharides of Salmonella species grown at low temperature. Identification and position. Eur J Biochem 130:167–171
Wollenweber HW, Seydel U, Lindner B, Lüderitz O, Rietschel ETh (1984) Nature and location of amide-bound (R)-3-acyloxyacyl groups in lipid A of lipopolysaccharides from various gramnegative bacteria. Eur J Biochem 145:265–272
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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