Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: infection due to Enterococcus faecalis [ICD11:
XN2H4 
]
The structure was elucidated in this paperNCBI PubMed ID: 25421964Publication DOI: 10.1002/chem.201405857Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: Nifantiev NE <nen
ioc.ac.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russian Federation), Faculty of Chemistry, University of Gdansk Wita Stwosza 63, 80-308, Gdansk (Poland), Division of Pediatric Infectious Diseases, Hauner Childre n's Hospital Ludwigs-Maximilian University, Munich (Germany), Research Center Borstel, Leibniz-Center for Medicine and Biosciences Borstel (Germany)
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.
carbohydrates, conformation analysis, rearrangement, lactic acid, furanoside
Structure type: polymer chemical repeating unit
Location inside paper: p.1749, p.1752, fig.4, DHG
Trivial name: diheteroglycan (DHG)
Compound class: CPS
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, TLC, ESI-MS, conformation analysis, NMR-1D, HPLC, molecular modeling, MM3 force field, nOe, MD simulation
3D data: molecular modeling
NCBI Taxonomy refs (TaxIDs): 1351
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error