Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3).
The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1-->4)-galactosylation and high overall yields were achieved.
Pornsuriyasak
Papapida
P
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Blvd., St. Louis, MO 63121, USA.
Demchenko
Alexei V
AV
D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry*; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D055746:Stage-Specific Embryonic Antigens; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry
D015295:Antigens, Tumor-Associated, Carbohydrate; C472766:Gb3 antigen; D006028:Glycosphingolipids; D055746:Stage-Specific Embryonic Antigens; D013844:Thiazoles; C052924:stage-specific embryonic antigen-3