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.
The α-aminooxy derivative of the n class="Disease">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-thioglycosidedonor with N-hydroxysuccinimide. With access to α-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation.
Authors: Ravindra A De Silva; Qianli Wang; Tristan Chidley; Dananjaya K Appulage; Peter R Andreana Journal: J Am Chem Soc Date: 2009-07-22 Impact factor: 15.419
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