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AssigneeNational Research Council of Canada
InventorsUsha HEMRAZ, Sophie RÉGNIER, Edmond LAM, Vinicio VASQUEZ, Michael MCCLUSKIE, Felicity STARK, Bassel AKACHE
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A composition comprising a mixture of two or more stereoisomers of a synthetic charged isoprenoid glycolipid of Formula (I), or a pharmaceutically acceptable salt thereof, in which n is 0 or 1, R and R′ are independently hydrogen or hydroxyl, each Y is independently hydrogen or a sulfate group, and wherein at least one Y is a sulfate group, and less than 25% of the synthetic charged isoprenoid glycolipid molecules in the mixture comprise an archaeol moiety of the configuration (R)-2,3-bis(((3R,7R,11R)-3,7,11,15-tetramethylhexadecyl)oxy) propan-1-ol. Further provided are archaeosomes and immunogenic compositions comprising the composition, use of the composition as an adjuvant or immunostimulant, and processes for synthesizing the composition.
A composition comprising a mixture of two or more stereoisomers of a synthetic charged isoprenoid glycolipid comprising a sulfated saccharide group covalently linked to the free sn-1 hydroxyl group of the glycerol backbone of an archaeol moiety via a beta linkage, wherein the synthetic charged glycolipid is a compound of the formula:
A process for synthesizing a composition comprising a mixture of two or more stereoisomers of an archaeol, the process comprising treating (±)-3-benzyloxy-1,2-propanediol with a mesylated phytol derivative through a double nucleophilic substitution reaction, followed by a reductive debenzylation reaction,
A process for synthesizing a mixture of two or more stereoisomers of a synthetic charged isoprenoid glycolipid or a pharmaceutically acceptable salt thereof, the process comprising covalently linking a sulfated saccharide group of the formula:
Dependencies are inferred from the claim text.