191
Different methods have been used for the synthesis of carbohydrate antigen protein neoglycoconjugates. One of these methods consisted of the use of the squaric
acid chemistry for the single-point attachment of carbohydrates to proteins [45–48].
Tietze et al. used squaric acid diethyl esters for the conjugation [46], while it has
also been reported that squaric acid dimethyl esters [49, 50], as well as didecyl
squarate [51], were used for the single point attachment of carbohydrates to proteins. In addition, Kamath et al. used squaric acid amide ethyl esters for the conjugation of oligosaccharides to protein. They monitored the conjugation using
matrix-assisted laser desorption ionization-time of flight mass spectrometry
(MALDI-TOF-MS) [52].
More recently, the group of Kováč also utilized the squaric acid chemistry to
conjugate different carbohydrate antigens to a protein carrier [53–55]. They used
this strategy to conjugate the synthetic tetrasaccharide side chain of the Bacillus
anthracis exosporium to the bovine serum albumin (BSA) protein [54].
Fig. 11.2 Generation of the immune responses against oligosaccharide antigen-carrier protein
conjugate vaccines [40]
Fig. 11.3 Composition of the
neoglyco conjugate vaccine
11 Defense Against Biological Terrorism: Vaccines and Their Characterizations
Different methods have been used for the synthesis of carbohydrate antigen protein neoglycoconjugates. One of these methods consisted of the use of the squaric
acid chemistry for the single-point attachment of carbohydrates to proteins [45–48].
Tietze et al. used squaric acid diethyl esters for the conjugation [46], while it has
also been reported that squaric acid dimethyl esters [49, 50], as well as didecyl
squarate [51], were used for the single point attachment of carbohydrates to proteins. In addition, Kamath et al. used squaric acid amide ethyl esters for the conjugation of oligosaccharides to protein. They monitored the conjugation using
matrix-assisted laser desorption ionization-time of flight mass spectrometry
(MALDI-TOF-MS) [52].
More recently, the group of Kováč also utilized the squaric acid chemistry to
conjugate different carbohydrate antigens to a protein carrier [53–55]. They used
this strategy to conjugate the synthetic tetrasaccharide side chain of the Bacillus
anthracis exosporium to the bovine serum albumin (BSA) protein [54].
Fig. 11.2 Generation of the immune responses against oligosaccharide antigen-carrier protein
conjugate vaccines [40]
Fig. 11.3 Composition of the
neoglyco conjugate vaccine
11 Defense Against Biological Terrorism: Vaccines and Their Characterizations