A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues.
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.
Stadelmaier
A
A
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Figueroa-Perez
I
I
Deininger
S
S
von Aulock
S
S
Hartung
T
T
Schmidt
R R
RR
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D016207:Cytokines / Q000096:biosynthesis / Q000187:drug effects; D004075:Diglycerides / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007962:Leukocytes / Q000187:drug effects; D008070:Lipopolysaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D013211:Staphylococcus aureus / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013682:Teichoic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D016207:Cytokines; D004075:Diglycerides; D008070:Lipopolysaccharides; D013682:Teichoic Acids; C009900:lipoteichoic acid