Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
Organ / tissue: cell wallAssociated disease: tuberculosis [ICD11:
XN1N2 
];
infection due to Mycobacterium tuberculosis [ICD11:
XN1N2 ]
NCBI PubMed ID: 26195010Publication DOI: 10.1021/acs.joc.5b00964Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: s.hotha
iiserpune.ac.in
Institutions: Department of Chemistry, Indian Institute of Science Education and Research, Pune, India, Molecular Modelling Group, Indian Institute of Chemical Technology, Hyderabad, India
The occurrence of arabinofuranosides on the cell surface of Mycobacterium tuberculosis (Mtb) and their significance in controlling disease spurred interest in developing strategies for their diastereoselective synthesis. Mtb uses enzymes to achieve diastereoselectivity through noncovalent interactions. Of the two possible glycosidic linkages, chemically, 1,2-trans linkage is relatively easy to synthesize by taking advantage of neighboring group participation, whereas synthesis of the 1,2-cis linkage is notoriously difficult. In this article, stereochemical effects on the diastereoselectivity of arabinofuranosidation are investigated with thiopyridyl, imidate, and thiotolyl donors as well as differently crowded glycosyl acceptors; subtle differences in the stereochemical environment of the acceptors were observed to alter the diastereoselectivity of the furanoside formation. Results from this endeavor suggest that 1,2-cis arabinofuranosides can be synthesized conveniently by conducting the reaction at lower temperature on sterically demanding and less reactive substrates
cell wall, Mycobacterium tuberculosis, stereochemistry, arabinofuranosides
Structure type: oligomer
Location inside paper: Fig. 1
Aglycon: (->5) cell wall
Compound class: arabinan
Contained glycoepitopes: IEDB_1309625,IEDB_134619,IEDB_857717,IEDB_857718
Methods: 13C NMR, 1H NMR, IR, TLC, chemical synthesis, UV, optical rotation measurement, ESI-TOF-MS, UPLC-MS
Synthetic data: chemical
NCBI Taxonomy refs (TaxIDs): 1773Reference(s) to other database(s): GTC:G46014AY
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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