ERA is in the process of being migrated to Scholaris, a Canadian shared institutional repository service (https://scholaris.ca). Deposits to existing ERA collections are frozen until migration is complete. Please contact erahelp@ualberta.ca for further assistance
- 215 views
- 184 downloads
A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent Lipopolysaccharide
-
- Author(s) / Creator(s)
-
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.
-
- Date created
- 2019-01-27
-
- Subjects / Keywords
-
- Type of Item
- Article (Published)