Beilstein J. Org. Chem.2020,16, 1955–1962, doi:10.3762/bjoc.16.162
problematic synthesis of monophosphorylated mono- and disaccharide lipid X using a combination of established chemistry and a novel 2-naphthylmethylether (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
; lipid X; lipopolysaccharide; 2-naphthylmethylether; 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
. More importantly, we employed the 2-naphthylmethylether (Nap) group for protection of various hydroxy groups on the carbohydrate and acyl moieties, aiming to provide an advantage over previous methods that mainly used the benzyl group [4][14][15][16] in synthesizing lipid A derivatives. We also aim at
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Graphical Abstract
Figure 1:
Chemical structures of hexa-acylated Escherichia coli lipid A, monophosphorylated lipid X (the redu...