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 β-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.
Original language | English (US) |
---|---|
Pages (from-to) | 6239-6254 |
Number of pages | 16 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 14 |
Issue number | 18 |
DOIs | |
State | Published - Sep 15 2006 |
Externally published | Yes |
Keywords
- Bacteria
- Bisamphiphilic
- Cytokine release
- Gram-positive
- Lipoteichoic acid
- Synthesis
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry