title: Chemical Synthesis of the Tumor-Associated Globo H Antigen.
abstract: A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, was synthesized by a convergent and efficient [3+2+1] strategy using various glycosylation methods. All glycosylation reactions afforded good to excellent yields and outstanding stereoselectivity, including the installation ofcisα-linked D-galactose and L-fucose. The longest linear sequence for this synthesis was 11 steps from a galactose derivative11to give an overall yield of 2.6%. The synthetic target had a free and reactive amino group at the glycan reducing end, facilitating its conjugation with other molecules for various applications.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Satadru S
authors.initials: SS
authors.lastname: Mandal
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Guochao
authors.initials: G
authors.lastname: Liao
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Zhongwu
authors.initials: Z
authors.lastname: Guo
keywords: cancer antigen; carbohydrate; convergent synthesis; globo H; oligosaccharide