Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 18, Pages 3371-3381Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b809090d
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Funding
- National Institutes of Health [GM061761]
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Tetra-acylated lipid As derived from Porphyromonas gingivalis LPS have been synthesized using it key disaccharide intermediate functionalized with levulinate (Lev), allyloxycarbonate (Alloc) and anomeric dimethylthexylsilyl (TDS) its orthogonal protecting groups and 9-fluorenylmethoxycarbamate (Fmoc) and azido as amino protecting groups. Furthermore, an efficient cross-metathesis hits been employed for the preparation Of the Unusual branched R-(3)-hydroxy-13-methyltetradecanic acid and (R)-3-hexadecanoyloxy-15-methylhexadecanoic acid of P. gingivalis lipid A. Biological studies have shown that the synthetic lipid As cannot activate human and Mouse TLR2 and TLR4 to produce cytokines. However, it hits been found that the Compounds are potent antagonist of cytokine secretion by human monocytic cells induced by enteric LPS.
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