A highly efficient synthetic strategy for polymeric support synthesis of Le(x), Le(y), and H-type 2 oligosaccharides.
The O-protecting groups Levulinoyl (Lev) and 9-fluroenylmethoxycarbonyl (Fmoc) offer an attractive set of orthogonal protecting groups which are compatible with base sensitive N-trichloroethoxylcarbonyl (Troc) group. B exploiting these orthogonal protecting groups and a novel phenolic ester linker, a series of oligosaccharide of biological importance, Le(x), H-type 2, and Le(y), were synthesized on the polytheylene glycol resin MPEG (Mw 5000). The products bearing a p-hydroxybenzyl group could be easily converted into glycosyl donors for further synthesis. Using this strategy, a spacer containing tumor antigen Le(y)-Lac hexasaccharide was described. The artificial spacer at the reducing end provides an opportunity for selective conjugation to an appropriate carrier protein for immunlogical studies.
Zhu
T
T
Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, USA.
Boons
G J
GJ
D000017:ABO Blood-Group System; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry / Q000276:immunology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D006031:Glycosylation; D007983:Lewis Blood Group Antigens; D016256:Lewis X Antigen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D011092:Polyethylene Glycols / Q000737:chemistry; D013329:Structure-Activity Relationship
D000017:ABO Blood-Group System; D015295:Antigens, Tumor-Associated, Carbohydrate; D007983:Lewis Blood Group Antigens; D016256:Lewis X Antigen; D009844:Oligosaccharides; D011092:Polyethylene Glycols; C028210:monomethoxypolyethylene glycol