Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant.
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.
Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft St, Toledo, OH 43606, USA. peter.andreana@utoledo.edu.
Jean Paul
JP
Bourgault
Kevin R
KR
Trabbic
Mengchao
M
Shi
Peter R
PR
Andreana
D000276:Adjuvants, Immunologic / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry* / Q000276:immunology
D000276:Adjuvants, Immunologic; D004187:Disaccharides; D011134:Polysaccharides