Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeatingunit [
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L-Rha-(1
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3)-
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L-Rha-(1
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3)-
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L-Rha-(1
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2)]
n. This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressingthe hypersensitive response (HR) and in inducing
PR-1 gene expression in
Arabidopsis thaliana.Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculationsrevealed that a coiled structure develops with increasing chain length of the oligosaccharide. This isassociated with increasing efficacy in HR suppression and
PR-1 gene expression. We therefore infer thatthe coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecularpattern (PAMP).