Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

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A novel convergent synthetic strategy for the construction of multicomponent color touch 7/97 self-adjuvanting lipopeptide vaccines was developed.A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses.The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support.Four copies of a group A streptococcal B cell epitope (J8) were wella color charm 050 cooling violet then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction.

The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.