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“…After conjugation to a protein, the latter compound generated a carbohydrate‐specific IgG response when injected in mice with Freund′s complete adjuvant 19. Furthermore, the chemical synthesis of an acetate‐protected GM2 amino acid conjugate has been reported as a building block for the preparation of multivalent vaccine constructs 21. It has been subsequently used for the stepwise assembly of a glycopeptidic structure carrying five or six different tumor‐associated carbohydrate antigens 22.…”
Section: Introductionmentioning
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“…After conjugation to a protein, the latter compound generated a carbohydrate‐specific IgG response when injected in mice with Freund′s complete adjuvant 19. Furthermore, the chemical synthesis of an acetate‐protected GM2 amino acid conjugate has been reported as a building block for the preparation of multivalent vaccine constructs 21. It has been subsequently used for the stepwise assembly of a glycopeptidic structure carrying five or six different tumor‐associated carbohydrate antigens 22.…”
Section: Introductionmentioning
“…Chemical synthesis can bestow flexibility in functionalizing the antigen for immunological investigations. Although GM2 glycans have been chemically synthesized previously, with the need for stereoselective sialylation and formation of branched glycans, its preparation in a conjugatable form is not a trivial task. Our synthetic target was the GM2 tetrasaccharide 1 , bearing a reducing end free amine, which was prepared by regioselective sialylation of the lactosyl diol acceptor 2 by sialyl donor 3 , followed by glycosylation of the 4′‐OH by galactosamine (GalN) donor 4 (Scheme ).…”
Section: Resultsmentioning
“…Reduction of the resultant olefin with concurrent benzyl ester cleavage provides the glycosylamino acid cassette. Since optically pure allyl glycine is commercially available, this method does not require the installation of a stereogenic center and is suitable for the preparation of glycosyl amino acids bearing large carbohydrate moiety such as Gb 3 [66,67], GM2 [68], and Globo-H [69]. Finally, we have developed a protocol ( c ) that allows for the amino acid functionality to be directly introduced using either a glycal epoxide [70] or trichloroacetimidate as a glycosyl donor [71] and hydroxynorleucine as the glycosyl acceptor in the presence of Lewis acid.…”
Section: Unimolecular Multivalent Vaccinesmentioning