93 research outputs found
Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions
Bacterial cell wall peptidoglycan (PGN) is a potent immunostimulator and immune adjuvant. The PGN of Gram-negative bacteria and some Gram-positive bacteria contain meso -diaminopimelic acid ( meso -DAP), and we have recently shown that the intracellular protein Nod1 is a PGN receptor and recognizes DAP-containing peptides. In this study, we achieved the synthesis of DAP-containing PGN fragments, including the first chemical synthesis of tracheal cytotoxin (TCT), GlcNAc-(Β1–4)-(anhydro)MurNAc- L -Ala-Γ- D -Glu- meso -DAP- D -Ala, and a repeating-unit of DAP-type PGN, GlcNAc-(Β1–4)-MurNAc- L -Ala-Γ- D -Glu- meso -DAP- D -Ala. For the synthesis of PGN fragments, we first established a new synthetic method for an orthogonally protected meso -DAP derivative, and then we constructed the glycopeptide structures. The ability of these fragments to stimulate human Nod1, as well as differences in Nod1 recognition of the variety of synthesized ligand structures were examined. The results showed that the substitution of the N terminus of iE-DAP is necessary for stronger Nod1 recognition, but the structure of the substituent seems not to be strictly recognized. The importance of the carboxyl group at the 2-position of DAP for human Nod1 stimulation was also shown.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/61332/1/10318_ftp.pd
ChemInform Abstract: A SIMPLE APPROACH TO THE SYNTHESIS OF A MEMBRANE TEICHOIC ACID FRAGMENT OF STAPHYLOCOCCUS AUREUS
ChemInform Abstract: SYNTHESIS OF ALKYLOXAZOLINE DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE VIA PHOSPHATE INTERMEDIATES
ChemInform Abstract: SELECTIVE ALLYLATION OF SUGAR DERIVATIVES CONTAINING THE 1,1,3,3-TETRAISOPROPYLDISILOXANE-1,3-DIYL PROTECTIVE GROUP
Synthese eines 3-desoxy-D-manno-2-octulosonsäure(KDO)-haltigen tetrasaccharides und dessen strukturvergleich mit einem abbau- produkt aus bakterien-lipopolysacchariden
Oligosaccharides related to tumor-associate antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide ?-D-Galp-(1?3)-?-D-GalpNAc-(1?3)-?-D-Galp and of the Tetrasaccharide ?-L-Fucp-(1?2)-?-D-Galp-(1?3)-?-D-GalpNAc-(1?3)-?-D-Galp, components of a tumor antigen recognized by the antibody MBr1
Binding of heparan sulfate to fibroblast growth factor-2 total synthesis of a putative pentasaccharide binding site
High yielding allylation of a chiral secondary alcohol containing base sensitive functional groups
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