Taxonomic group: bacteria / Chlamydiae
(Phylum: Chlamydiae)
Associated disease: infection due to Chlamydia psittaci [ICD11:
XN4S7 
]
NCBI PubMed ID: 25354167Publication DOI: 10.1002/chem.201405424Publisher: Vch Verlagsgesellschaft
Correspondence: paul.kosma
boku.ac.at
Institutions: Department of Chemistry, University of Natural Resources and Life Sciences-Vienna, Muthgasse 18, 1190 Vienna (Austria)
A scalable approach towards high-yielding and (stereo)selective glycosyl donors of the 2-ulosonic acid Kdo (3-deoxy-D-manno-oct-2-ulosonic acid) is a fundamental requirement for the development of vaccines against Gram-negative bacteria. Herein, we disclose a short synthetic route to 3-iodo Kdo fluoride donors from Kdo glycal esters that enable efficient alpha-specific glycosylations and significantly suppress the elimination side reaction. The potency of these donors is demonstrated in a straightforward, six-step synthesis of a branched Chlamydia-related Kdo-trisaccharide ligand without the need for protecting groups at the Kdo glycosyl acceptor. The approach was further extended to include sequential iteration of the basic concept to produce the linear Chlamydia-specific α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo trisaccharide in a good overall yield.
carbohydrates, 3-deoxy-D-manno-oct-2-ulosonic acid, Kdo, Oligosaccharides, Chlamydia, glycosylation, immunochemistry, diastereoselectivity
Structure type: fragment of a bigger structure
Location inside paper: p.306
Trivial name: Chlamydia epitope
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_150901,IEDB_151769
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, ESI-TOF-MS
Related record ID(s): 11062, 11200
NCBI Taxonomy refs (TaxIDs): 83554Reference(s) to other database(s): GTC:G19436DI
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There is only one chemically distinct structure:
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