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Skip to Search Results- 8Todd L. Lowary
- 2Ryan P. Sweeney
- 1Akihiko Koizumi
- 1Antonio Molinaro
- 1Anushka B. Jayasuriya
- 1Claude Larrivée Aboussafy
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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
Download2019-01-27
Claude Larrivée Aboussafy, Lotte Bettina Anderson Gersby, Antonio Molinaro, Mari-Anne Newman, Todd L. Lowary
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...
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A Route to Polyprenol Pyrophosphate-Based Probes of O- Polysaccharide Biosynthesis in Klebsiella pneumoniae O2a
Download2019-01-27
Ryan P. Sweeney, Todd L. Lowary
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...
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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 fragments
Download2016-03-17
Todd L. Lowary, Roger A. Ashmus, George A. O'Doherty, Ying Jie Lim, Anushka B. Jayasuriya
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,...
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Development of an Orthogonal Protection Strategy for the Synthesis of Mycobacterial Arabinomannan Fragments
Download2015-10-28
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...
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Synthesis of a homologous series of galactofuranose-containing mycobacterial arabinogalactan fragments
Download2019-01-31
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...
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Synthesis of the Campylobacter jejuni 81-176 strain capsular polysaccharide repeating unit reveals the absolute configuration of its O-methyl phosphoramidate motif
Download2019-01-30
V. Narasimharao Thota, Michael J. Ferguson, Ryan P. Sweeney, Todd L. Lowary
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...
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2019-01-31
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...
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Synthetic Polyprenol-Pyrophosphate Linked Oligosaccharides Are Efficient Substrates for Mycobacterial Galactan Biosynthetic Enzymes
Download2019-01-31
Xiaochao Xue, Ruixiang Blake Zheng, Akihiko Koizumi, Ling Han, John S. Klassen, Todd L. Lowary
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...