title: Solution syntheses of protected type II Lewis blood group oligosaccharides: study for automated synthesis.
abstract: Glycosyl phosphate and trichloroacetimidate monosaccharide building blocks were used in a stepwise solution-phase synthesis of three Lewis blood group oligosaccharides. The syntheses were conducted to establish general routes for the automated assembly of the oligosaccharide portion of biologically important glycolipids. The H-type II pentasaccharide, Le(x) pentasaccharide, and Le(y) hexasaccharide were prepared in high yield. These syntheses served to evaluate the utility and limitations of the 2-(azidomethyl)benzoate ester (AZMB) for the construction of complex carbohydrates. Development of a glucosamine building block containing a N-trichloroacetamide group to mask the C2 amine improved coupling yields and was key for completion of the Le(x) and Le(y) structures.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
authors.forename: Kerry Routenberg
authors.initials: KR
authors.lastname: Love
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D000017:ABO Blood-Group System / Q000737:chemistry*; D002240:Carbohydrate Sequence; D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D006801:Humans; D007983:Lewis Blood Group Antigens / Q000737:chemistry; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
chemical_list: D000017:ABO Blood-Group System; D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides