Abstract
Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which d-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbohydrate Conformation
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Carbohydrate Sequence
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Cytokines / biosynthesis
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Cytokines / drug effects
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Diglycerides / chemistry*
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Dose-Response Relationship, Drug
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Humans
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Leukocytes / drug effects
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Lipopolysaccharides / chemical synthesis
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Lipopolysaccharides / chemistry*
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Lipopolysaccharides / pharmacology
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Molecular Conformation
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Molecular Sequence Data
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Staphylococcus aureus / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
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Teichoic Acids / chemical synthesis
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Teichoic Acids / chemistry*
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Teichoic Acids / pharmacology
Substances
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Cytokines
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Diglycerides
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Lipopolysaccharides
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Teichoic Acids
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lipoteichoic acid