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Issue 11, 2014
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Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant

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Abstract

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.

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

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Supplementary files

Article information


Submitted
18 Jan 2014
Accepted
20 Jan 2014
First published
29 Jan 2014

Org. Biomol. Chem., 2014,12, 1699-1702
Article type
Communication
Author version available

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

J. P. Bourgault, K. R. Trabbic, M. Shi and P. R. Andreana, Org. Biomol. Chem., 2014, 12, 1699
DOI: 10.1039/C4OB00128A

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