Chemical synthesis of an artifical antigen containing the trisaccharide hapten of mycobacterium leprae

Synthetic studies on calicheamicin γ1I—synthesis of(−)-calicheamicinone and models representing the four sugars and the aromatic system

“…At this point, the optical purity of the compound was confirmed by NMR comparison of its Mosher ester with corresponding material made from racemic 112. The C(3) hydroxy group was now protected as its pivaloyl ester, and dihydroxylation, under standard conditions, produced diol 118, which could be selectively and efficiently (95%) methylated 33 (Bu 2 SnO, MeI) on the C(3) oxygen (118 ? 119).…”

High Sensitive Detection of Carbohydrate Binding Proteins in an ELISA-Solid Phase Assay Based on Multivalent Glyconanoparticles

“…Soon afterwards, glycolipids were effectively employed to coat ELISA surfaces for a Mycobacterium leprae -specific serodiagnostic test [4–6]. With the identification and characterization of oligosaccharide antigen structures, chemical strategies were developed to conjugate the carbohydrate antigen to proteins (bovine or human serum albumin), polymers (acrylamide derivatives) [7,8] and dendrimers [9] in order to enhance the number carbohydrate epitopes on the ELISA surface and improve the sensitivity of the assay. The relatively recent introduction of glycan microarray technology also provided a platform for high throughput screening, yielding information about the specificity of glycan-binding proteins [10,11].…”

Synthesis of the pentasaccharide repeating unit fromRuminococcus gnavusand measurement of its inflammatory properties

“…Acceptor 4 was prepared by selective protection of the equatorial C3 hydroxyl on 9 (ref. 15 ) ( Scheme 2 ) using dibutyltin oxide and para -methoxybenzyl chloride (PBMCl). Donor 3, prepared using the procedure reported by Chu, et al , 16 was activated using the Crich 17 method and coupled with 4 to give 5.…”