The biological importance of lipopolysaccharides (LPS), component of  bacterial cell wall has not been explained sufficiently. The glycine epitope present in these structures could play an important role in the immunological response after bacterial infections,  during sepsis and septic shock. Modified thioglycosides conjugated with glycine residue could be used for broadly reactive antibodies production which would be able to neutralize endotoxin biological activity.

Previously, in our studies we obtained synthetic and stable substituted N-acetylated glycine 1-thioglycosides as amine functional group derivatives of monosaccharides, e.g., D-glucose or D-galactose as well as disaccharides, e.g., melibiose, lactose or maltose. The conditions of aminoacylation rections were validated and specific products were separeted by using chromatography methods. Their structures were confirmed by NMR.

Next, these model aminoacylated sugar structures were conjugated with two different carrier proteins e.g. bovine serum albumin (BSA) and horse myoglobin (MYO) to obtain reactive antibodies after experimental animals immunization. In order to obtain carrier proteins capable to bind the sugar ligand- amine containing group, BSA and MYO were modified by using glycidol to introduce aldehyde functional groups. In these experiments we used monomeric BSA as a result of purification of commercial material. Treatment of the stable protein-diol intermediates after glycidol application with sodium periodate resulted in the generation of reactive aldehyde functionalities through the oxidation of the glycol moieties.

Modified and formylated carrier proteins were conjugated with aminoacylated thioglicosides in the presence of sodium cyanoborohydride in order to complete reduce of the labile Schiff base intermediate to a chemically stable bond between aldehyde and amine functional groups. Subsequently, obtained products were separated by using HW-55S size-exclusion chromatography and analyzed in SDS-PAGE.

The presence of aminoacylated glycoconjugates fractions were expected in protein immunoblot with specific anti-aminoacylated antibodies obtained after rabbit immunization with Escherichia coli K12 C600 core oligosaccharide glycine-containing glyconjugate. Received glycine-acylated glycoconjugates as one of the  non-sugar substituents localized in various bacterial LPS as an inherent component, can mimic common epitopes in different bacterial endotoxins responsible for sepsis development and propagation. These synthetic compounds could be used as glycoconjugate vaccines in protection against  serious bacterial infections.

Research studies are part-financed by Ministry of Science and Higher Education of Poland (Grant No. N N209 186338) as well as European Union (POIG.01.01.02-02-003/08-00) and (POKL.08.02.02-02-001/10).  

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