Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 27312264Publication DOI: 10.1002/chem.201601284Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: corsaro
unina.it; ebedini
unina.it
Institutions: Department of Experimental Medicine, Second University of Naples, via de Crecchio 7, 80138, Naples, Italy, Department of Biology, University 'Roma Tre', Viale G. Marconi 446, 00146, Rome, Italy, Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, CF10 3AT, Cardiff, The United Kingdom, Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, 80126, Naples, Italy
A semisynthetic approach to novel lipid A derivatives from Escherichia coli (E. coli) lipid A is reported. This methodology stands as an alternative to common approaches based exclusively on either total synthesis or extraction from bacterial sources. It relies upon the purification of the lipid A fraction from fed-batch fermentation of E. coli, followed by its structural modification through tailored, site-selective chemical reactions. In particular, modification of the lipid pattern and functionalization of the phosphate group as well as of the sole primary hydroxyl group were accomplished, highlighting the unusual reactivity of the molecule. Preliminary investigations of the immunostimulating activity of the new semisynthetic lipid A derivatives show that some of them stand out as promising, new immunoadjuvant candidates.
carbohydrates, Escherichia coli, immunology, lipids, glycolipids, Synthetic methods, immunoadjuvant
Structure type: oligomer
Location inside paper: p.11054, fig.1, structure 1
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, TLC, 31P NMR, chemical synthesis, MALDI-TOF MS, immunological assays
Related record ID(s): 11768
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
There is only one chemically distinct structure:
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