Beilstein J. Org. Chem.2020,16, 1955–1962, doi:10.3762/bjoc.16.162
problematic synthesis of monophosphorylated mono- and disaccharide lipidX using a combination of established chemistry and a novel 2-naphthylmethyl ether (Nap) protecting group for “permanent” protection of hydroxy groups. Of particular note is the fact that the key Nap protecting group is able to remain in
; lipidX; lipopolysaccharide; 2-naphthylmethyl ether; synthesis; Introduction
Bacterial cell surfaces are decorated with various types of glycoconjugates (in the form of glycoproteins and glycolipids) that are known to participate in many biological processes, especially in the interactions between
][8][9].
Various lipid A derivatives have since been synthesized to dissociate endotoxic effects from beneficial immunomodulatory activities. LipidX, 2-N;3-O-di[(R)-3-hydroxytetradecanoyl]-ᴅ-glucosamine-1-phosphate, is the naturally occurring early monosaccharide precursor of lipid A biosynthesis
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Graphical Abstract
Figure 1:
Chemical structures of hexa-acylated Escherichia coli lipid A, monophosphorylated lipid X (the redu...