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- W2055260115 abstract "Abstract Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1,4′-bisphosphoryl as well as the related 4′-monophosphoryl derivatives of lipid A were synthesized. (R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3′ and N-acylated with (R)-3-hydroxyicosanoic acid at both glucosamine units. Efficient purification methods for highly hydrophobic long-chain tri-, tetra- and pentaacyl progenitors of lipid A have been developed. Purity and homogeneity of the synthetic target compounds were confirmed by NMR and MS-data as well as a sensitive immunostaining approach. The tetra- and pentaacyl species serve as biomedical probes to investigate the endotoxic potential of chlamydial lipid A and to clarify its role in Chlamydia associated infections." @default.
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- W2055260115 date "2004-12-01" @default.
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- W2055260115 title "Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid" @default.
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- W2055260115 doi "https://doi.org/10.1016/j.tet.2004.10.017" @default.
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