Abstract
Two analogues of the Sd a determinant tetrasaccharide have been synthesized in order to investigate the physiological role of this carbohydrate moiety. These saccharides, having two different anionic substitutes for the sialic acid residue, are: β- d-Gal p NAc-(1 → 4)-3-O- SO 3H -β- d-Gal p-(1 → 4)-β- d-Glc p NAc-(1 → O)( CH 2 ) 5NH 2 and β- d-Gal p NAc-(1 → 4)-3-O- CH 2COOH -β- d-Gal p-(1 → 4)-β- d-Glc p NAc-(1 → 0) (CH 2) 5NH 2 . 5-Azidopentyl (2,6- di-O- benzyl-β- d-galactopyranosyl )-(1 → 4)-3,6- di-O- benzyl-2- deoxy-2- phthalimido-β- d-glucopyranoside served as a general building block. The trisaccharides were obtained after prior selective derivatization of HO-3′ of the disaccharide derivative via a dibutyltin oxide mediated reaction, followed by coupling at HO-4′ with 3,4,6- tri-O- acetyl-2- deoxy-2- phthalimido-β- d- galactopyranosyl trichloroacetimidate, and processing of the formed trisaccharide derivatives into their free forms. Two analogues of the Sd a determinant tetrasaccharide have been synthesized aimed at the investigation of the physiological role of this carbohydrate moiety. These saccharides, having two different anionic substitutes for the sialic acid residue, are; β- d-Gal p NAC-(1 → 4)-3-O- SO 3H -β- d-Gal p-(1 → 4)-β- d-Glc p NAC-(1 → O) (CH 2) 5NH 2 and β- d-Gal p NAC-(1 → 4)-3-O- CH 2COOH -β- d-Gal p-(1 → 4)-β- d-Glc p NAC-(1 → O) (CH 2) 5NH 2 .
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