Synthesis of type 2 Lewis antigens via novel regioselective glycosylation of an orthogonally protected lactosamine diol derivative. (3rd March 2016)

• Record Type: Journal Article
• Authors: Yamazaki, Yuji; Sezukuri, Kyohei; Takada, Junko; Obata, Hiroaki; Kimura, Shunsaku; Ohmae, Masashi
• Is Part Of: Carbohydrate research. Volume 422(2016)
• Page Start: 34
• Page End: 44
• Publication Date: 2016-03-03
• Subjects: Type 2 Lewis antigens -- Sulfated Lewis x -- Lewis y -- Regioselective glycosylation -- The Heyns rearrangement; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2016.01.003
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: A facile and rapid synthesis of type 2 Lewis antigens is demonstrated. A newly designed diol acceptor shows unique reactivity of 3-OH > 2′-OH. On-demand synthesis of Le x and Le y is achieved with this new diol acceptor. Synchronous synthesis of Le x and Le y is performed in this study for the first time. Graphical abstract: 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.