Towards the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks.
Towards the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks.
复制标题
DOI：
10.1016/j.tet.2010.03.077
复制
发表时间：
2010-05-29
期刊：
影响因子：
2.1
通讯作者：
Suda Y
中科院分区：
文献类型：
--
作者：
Saito A;Wakao M;Deguchi H;Mawatari A;Sobel M;Suda Y
以葡萄糖胺盐酸盐和葡萄糖醛酸-6，3-内酯为起始原料，合成了肝素（HP）和硫酸乙酰肝素（HS）中的单糖、葡萄糖胺和两种糖醛酸（葡萄糖醛酸和艾杜糖醛酸）。在二糖结构单元的合成中，制备糖醛酸（葡萄糖醛酸和艾杜糖醛酸部分）的关键问题分别在12个步骤和15个步骤中实现，而没有繁琐的C-6氧化。将所得单糖部分用于合成具有葡糖胺-葡糖醛酸（GlcN-GlcA）或艾杜糖醛酸（GlcN-IdoA）序列的HP/HS二糖结构单元。二糖结构单元也适合于进一步修饰，例如糖基化、选择性脱保护和硫酸化。
The monosaccharide moieties found in heparin (HP) and heparan sulfate (HS), glucosamine and two kinds of uronic acids, glucuronic and iduronic acids, were efficiently synthesized by use of glucosamine hydrochloride and glucurono-6,3-lactone as starting compounds. In the synthesis of the disaccharide building block, the key issues of preparation of uronic acids (glucuronic acid and iduronic acid moieties) were achieved in 12 steps and 15 steps, respectively, without cumbersome C-6 oxidation. The resulting monosaccharide moieties were utilized to the syntheses of HP/HS disaccharide building blocks possessing glucosamine-glucuronic acid (GlcN-GlcA) or iduronic acid (GlcN-IdoA) sequences. The disaccharide building blocks were also suitable for further modification such as glycosylation, selective deprotection, and sulfation.
登录
查看更多内容
影响因子：
4
作者：
de Paz, Lose L.;Moseman, E. Ashley;Seeberger, Peter H.
通讯作者：
Seeberger, Peter H.
影响因子：
15.9
作者：
Esko, JD;Lindahl, U
通讯作者：
Lindahl, U
影响因子：
15
作者：
de Paz, JL;Noti, C;Seeberger, PH
通讯作者：
Seeberger, PH
影响因子：
14.8
作者：
Gama, Cristal I.;Tully, Sarah E.;Hsieh-Wilson, Linda C.
通讯作者：
Hsieh-Wilson, Linda C.
影响因子：
4.4
作者：
Hecht, Marie-Lyn;rosental, Benyamin;Seeberger, Peter H.
通讯作者：
Seeberger, Peter H.