Glycobiology Advance Access published online on May 24, 2004
Glycobiology, doi:10.1093/glycob/cwh096
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1 Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia 4, 80126 Napoli, Italy
* To whom correspondence should be addressed. E-mail: molinaro{at}unina.it.
For the first time, the complete structure of the lipid A from the lipopolysaccharide of an Agrobacterium species is here reported. In particular, the structure of the lipid A from Agrobacterium tumefaciens strain C58, a soil pathogen bacterium strictly related to Rhizobiaceae, was determined. The structural study, carried out by chemical analysis, MS spectrometry and NMR spectroscopy, revealed that lipid A fraction consisted of a mixture of species all sharing the bis-phosphorylated glucosamine disaccharide backbone and that could be designated, according to the acylation pattern, in two main structural motifs. The main species was a penta-acylated lipid A bearing two unsubstituted 14:0 (3-OH) fatty acids in ester linkage and two 16:0 (3-OH) in amide linkage, the one on GlcN II was O-acylated by a long chain fatty acid, 28:0 (27-OH). This, in turn, was esterified by a 3-hydroxy-butyroyl residue at its hydroxy group. The second species, in lesser amount, was identified as a tetra-acylated lipid A and lacked of 14:0 (3-OH) residue on GlcN I. Other species, deriving from these two, lacked a phosphate group or 3-hydroxy-butyroyl residue otherwise carried a 26:0 (25-OH) as long chain fatty acid. The lipid A structure of the phytopathogen Agrobacterium tumefaciens strain C58 presents deep structural analogies with lipid A of symbiotic Rhizobium and the hypothesis is advanced that it can be a strategy of the bacterium to escape or attenuate the plant response.
Revised May 12, 2004
Accepted May 12, 2004
ORIGINAL ARTICLES
Full structural characterization of the lipid A components from the Agrobacterium tumefaciens strain C58 lipopolysaccharide fraction
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