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A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide
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- Author(s) / Creator(s)
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The synthesis of bradyrhizose, the monosaccharide component of the lipopolysaccharide O-antigen of the nitrogen-fixing bacteria Bradyrhizobium sp. BTAi1 and sp. ORS278, has been achieved in 25 steps in an overall yield of 6% using myo-inositol and ethyl propiolate as the starting materials. The route involved the late state resolution of a racemic intermediate to provide both enantiomers of this unusual bicyclic monosaccharide. Both the natural D-enantiomer, and the unnatural and heretofore unknown L-enantiomer, were converted to disaccharide derivatives containing different forms of the monosaccharide (D,D; L,L; D,L; L,D). Evaluation of the synthetic compounds for their ability to act as microbe-associated molecular patterns in plants, through induction of reactive oxygen species, was investigated. These experiments suggest that the immunologically-silent nature of the natural glycans is due to specific structural features.
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- Date created
- 2019-01-27
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- Type of Item
- Article (Published)