Toward the construction of dermatan sulfate (DS) partial disaccharide library: efficient synthesis of building blocks, common intermediate, and ligand conjugate of type-B DS disaccharide

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• 作者：Yuhei Kakitsubata^a ; Rikiya Aramaki^a ; Kyosuke Nishioka^a ; Masahiro Wakao^a ; ^{wakao@eng.kagoshima-u.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Yasuo Suda^a ; ^b
• 关键词：Dermatan sulfate ; Synthesis ; Library ; Glycosaminoglycan
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：9 March 2016
• 年：2016
• 卷：57
• 期：10
• 页码：1154-1157
• 全文大小：498 K

文摘

Dermatan sulfate (DS) is composed of a repeating disaccharide unit containing iduronic acid (IdoA) and N-acetylgalactosamine (GalNAc). In the divergent synthesis of DS disaccharide, it is important to prepare the IdoA moiety with a diverse set of protecting groups. IdoA was efficiently obtained from glucose in 20 steps with some modifications following the method reported by van Boeckel et al. A disaccharide building block for constructing the DS disaccharide was synthesized by the glycosylation of the designed IdoA moiety with GalNAc. The disaccharide building block was used in the synthesis of DS-B disaccharide and its ligand conjugate.