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Definitive Structural Assessment of Enterococcal Diheteroglycan Full article

Journal Chemistry: A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765
Output data Year: 2015, Volume: 21, Number: 4, Pages: 1749-1754 Pages count : 6 DOI: 10.1002/chem.201405857
Authors Krylov Vadim B. 1 , Gerbst Alexey G. 1 , Argunov Dmitry A. 1 , Dmitrenok Andrey S. 1 , Shashkov Alexander S. 1 , Kaczynski Zbigniew 2 , Huebner Johannes 3 , Holst Otto 4 , Nifantiev Nikolay E. 1
Affiliations
1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russian Federation)
2 Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk (Poland)
3 Division of Pediatric Infectious Diseases, Hauner Children's Hospital, Ludwigs-Maximilian University, Munich (Germany)
4 Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel (Germany)

Abstract: Enterococcus faecalis is one of most important nosocomial and often multi-antibiotic resistant pathogens responsible for infections that are difficult to treat. Previously, a cell-wall polysaccharide termed diheteroglycan (DHG) was isolated and characterized as a promising vaccine candidate. However, the configuration of its lactic acid (LA) residue attached to the galactofuranoside unit was not assessed, although it influences conformation of DHG chain in terms of biological recognition and immune evasion. This study proves the R configuration of the LA residue by means of chemical analysis, investigation of intramolecular NMR nuclear Overhauser effects and molecular dynamics simulations of native DHG and corresponding R and S models, which were obtained by using pyranoside-into-furanoside rearrangement. As alternative treatment and prevention strategies for E. faecalis are desperately needed, this discovery may offer the prospect of a synthetic vaccine to actively immunize patients at risk.
Cite: Krylov V.B. , Gerbst A.G. , Argunov D.A. , Dmitrenok A.S. , Shashkov A.S. , Kaczynski Z. , Huebner J. , Holst O. , Nifantiev N.E.
Definitive Structural Assessment of Enterococcal Diheteroglycan
Chemistry: A European Journal. 2015. V.21. N4. P.1749-1754. DOI: 10.1002/chem.201405857 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000347841500046
≡ Scopus: 2-s2.0-84920964544
≡ OpenAlex: W2073034085
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