title: Synthesis of type 2 Lewis antigens via novel regioselective glycosylation of an orthogonally protected lactosamine diol derivative.
abstract: The novel and efficient synthesis of type 2 Lewis antigens is reported in this study. The rationally designed lactosamine-3,2'-diol derivative with an orthogonal set of protecting groups is efficiently glycosylated with a benzyl protected 1-thio-l-fucoside donor in a unique regioselective manner to produce Lewis x (Le(x)) and Lewis y (Le(y)) derivatives in good yields. These derivatives can be prepared not only exclusively but also synchronously by choosing the appropriate reaction temperature and donor-acceptor molar ratio. The Le(x) derivatives are easily converted into sulfated or non-sulfated Le(x) bearing a terminal azido functionalized oligo-(ethyleneoxide) linker; the Le(y) derivative having the same linker can also be prepared, all of which can be further used for the chemical modification of other compounds and materials.
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Yuji
authors: Y
authors: Yamazaki
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Kyohei
authors: K
authors: Sezukuri
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Junko
authors: J
authors: Takada
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Hiroaki
authors: H
authors: Obata
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Shunsaku
authors: S
authors: Kimura
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan. Electronic address: ohmae@peptide.polym.kyoto-u.ac.jp.
authors: Masashi
authors: M
authors: Ohmae
mesh_terms: D000606:Amino Sugars / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D006018:Glycols / Q000737:chemistry*; D006031:Glycosylation; D007700:Kinetics; D007983:Lewis Blood Group Antigens / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D001386:Azides; D006018:Glycols; D007983:Lewis Blood Group Antigens; C032233:lactosamine
keywords: Lewis y; Regioselective glycosylation; Sulfated Lewis x; The Heyns rearrangement; Type 2 Lewis antigens