Solution syntheses of protected type II Lewis blood group oligosaccharides: study for automated synthesis.
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.
Love
Kerry Routenberg
KR
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Seeberger
Peter H
PH
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
D000017:ABO Blood-Group System; D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides