Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: nosocomial infections [ICD11:
XB25 
];
osteomyelitis [ICD11:
FB84 ];
infection due to Acinetobacter baumannii [ICD11:
XN8LS ]
The structure was elucidated in this paperNCBI PubMed ID: 34665908Publication DOI: 10.1002/chem.202103234Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: Peter.Seeberger
mpikg.mpg.de
Institutions: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476, Potsdam, Germany
Acinetobacter baumannii is an opportunistic pathogen that causes serious nosocomial infections. One of the multidrug-resistant strains, AB5075, can result in bacteremia, pneumonia and wound infections associated with high morbidity and mortality. The structurally unique glycans on the surface of these bacteria are attractive targets for the development of glycoconjugate vaccines. Here, we report the first total synthesis of the densely functionalized trisaccharide repeating unit of A. baumannii AB5075 as well as two analogues. The construction of 1,2-cis linkages between the rare sugars relies on a double-serial inversion strategy. The judicious selection of building blocks and reaction conditions allowed for stereoselective glycosylations, the installation of acetamido groups and the (S)-3-hydroxybutanoyl chain.
carbohydrates, Acinetobacter baumannii, Oligosaccharides, vaccines, Amides, total synthesis
Structure type: oligomer
Location inside paper: p. 17445, Fig. 1(A)
Aglycon: (1->1) 5-aminopentyl
Compound class: CPS
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, FTIR, glycosylation
Synthetic data: chemical
Comments, role: repeating unit of A. baumannii AB5075.
Related record ID(s): 10980
NCBI Taxonomy refs (TaxIDs): 1116234
Show glycosyltransferases
There is only one chemically distinct structure:
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