Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.
synthesis, serotype, trisaccharide, vaccine, Plesiomonas shigelloides, total synthesis, carbohydrate chemistry
NCBI PubMed ID: 29377682Publication DOI: 10.1021/jacs.8b00148Journal NLM ID: 7503056Publisher: American Chemical Society
Correspondence: peter.seeberger@mpikg.mpg.de; jianyin@jiangnan.edu.cn
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces , Am Muhlenberg 1, 14476 Potsdam, Germany, Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University , Wuxi, Jiangsu Province 214122, P.R. China
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, chemical methods, glycosylation
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