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- 8Todd L. Lowary
- 2Ryan P. Sweeney
- 1Akihiko Koizumi
- 1Antonio Molinaro
- 1Anushka B. Jayasuriya
- 1Claude Larrivée Aboussafy
- 1Capsular polysaccharide
A Convergent Route to Enantiomers of the Bicyclic Monosaccharide Bradyrhizose Leads to Insight into the Bioactivity of an Immunologically Silent LipopolysaccharideDownload
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...
A Route to Polyprenol Pyrophosphate-Based Probes of O- Polysaccharide Biosynthesis in Klebsiella pneumoniae O2aDownload
An approach for the assembly of polyprenol pyrophosphate-based probes of O-polysaccharide biosynthesis in Klebsiella pneumoniae serotype O2a is described. This convergent route features high yielding, diastereoselective glycosylations and the late stage installation of the polyprenol...
De novo asymmetric synthesis of a 6-O-methyl-D-glycero-L- gluco-heptopyranose-derived thioglycoside for the preparation of Campylobacter jejuni NCTC11168 capsular polysaccharide fragmentsDownload
An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-D-glycero- L-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably,...
Development of an Orthogonal Protection Strategy for the Synthesis of Mycobacterial Arabinomannan FragmentsDownload
Mycobacterium tuberculosis, the organism that causes tuberculosis (TB), has a carbohydrate-rich cell wall structure that possesses a number of immunogenic antigens. Circulating antibodies that recognize these glycans are present in patients infected by mycobacteria; detection of these antibodies...
Synthesis of a homologous series of galactofuranose-containing mycobacterial arabinogalactan fragmentsDownload
Mycobacteria, including the human pathogen Mycobacterium tuberculosis the causative agent of tuberculosis, produce a complex cell wall structure made of carbohydrates and lipids. The major structural element of the mycobacterial cell wall is a glycoconjugate called the mycolic...
Synthesis of the Campylobacter jejuni 81-176 strain capsular polysaccharide repeating unit reveals the absolute configuration of its O-methyl phosphoramidate motifDownload
The O-methyl phosphoramidate (MeOPN) motif is a non-stoichiometric modification of capsular polysaccharides (CPS) in ~70% of all Campylobacter jejuni strains. Infections by C. jejuni lead to food-borne illnesses and the CPS they produce are key virulence factors. The MeOPN phosphorus atom in...
Chlorella viruses produce N-linked glycoproteins with carbohydrate moieties that differ in structure from all other N- linked glycans. In addition, unlike most viruses, these organisms do not hijack the biosynthetic machinery of the host to make glycocoproteins; instead, they produce their own...
Synthetic Polyprenol-Pyrophosphate Linked Oligosaccharides Are Efficient Substrates for Mycobacterial Galactan Biosynthetic EnzymesDownload
Mycobacteria, including the human pathogen Mycobacterium tuberculosis, produce a complex cell wall that is critical for their survival. The largest structural component of the cell wall, the mycolylarabinogalactanpeptidoglycan complex, has at its core a galactan domain composed of...