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Synthesis of the tumor associative ?-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant.

ABSTRACT: The ?-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a D-GalN3 acceptor carrying a pre-installed ?-N-hydroxysuccinimidyl moiety. The natural ? linkage was prepared in high selectivity employing a suitably protected D-GalN3-thioglycoside donor with N-hydroxysuccinimide. With access to ?-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation.

SUBMITTER: Bourgault JP

PROVIDER: S-EPMC3956868 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant.

Bourgault Jean Paul JP Trabbic Kevin R KR Shi Mengchao M Andreana Peter R PR

Organic & biomolecular chemistry 20140301 11

The α-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a D-GalN3 acceptor carrying a pre-installed α-N-hydroxysuccinimidyl moiety. The natural α linkage was prepared in high selectivity employing a suitably protected D-GalN3-thioglycoside donor with N-hydroxysuccinimide. With access to α-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation. ...[more]

PMID: 24473737

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