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Synthesis of lipid A and its analogs and conjugates

Lipid A is the innermost glycolipid component of bacterial lipopolysaccharide endotoxin, a major component of gram-negative bacteria outer cell membrane. Since the discovery of its immune stimulating property, lipid A has attracted much attention from immunotherapists as well as synthetic chemists. A variety of lipid A derivatives and analogs with variations in lipid chains, carbohydrate rings and/or phosphates of the conservative core structure have been synthesized and investigated as vaccine carriers or adjuvants. This chapter summarizes the previous accomplishments of chemists in advancing the synthesis of lipid A by focusing on the overall synthetic strategy, protection tactic, and phosphorylation and acylation methodologies, to provide guidelines for future synthetic studies in this area. Enzymatic synthesis of lipid A and chemical synthesis of simplified lipid A mimics are also briefly discussed at the end.

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06 Oct 2020
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From the book series:
SPR - Carbohydrate Chemistry