Preparation and biological activity of N-sulfonated chondroitin and dermatan sulfate derivatives

Preparation and biological activity of N-sulfonated chondroitin and dermatan sulfate derivatives
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DOI:
10.1016/0008-6215(96)00129-2
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发表时间:
1996-08-26
影响因子:
3.1
通讯作者:
Linhardt, RJ
Linhardt, RJ
中科院分区:
化学3区
文献类型:
--
作者:
Nadkarni, VD;Toida, T;Linhardt, RJ

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硫酸软骨素和硫酸皮肤素是结构复杂的硫酸化线性多糖家族,称为糖胺聚糖(GAG),糖醛酸和N-乙酰化D-半乳糖胺残基交替[1](方案1)。硫酸软骨素A(1A)由未硫酸化的D-葡萄糖醛酸1--* 3连接到N-乙酰化的4-硫酸化D-半乳糖胺,后者又通过1~ 4键连接到下一个D-葡萄糖醛酸残基。硫酸软骨素C(1B)在N-乙酰化的D-半乳糖胺上有一个6-硫酸酯基,取代了硫酸软骨素A中的4-硫酸酯基。硫酸皮肤素,也称为硫酸软骨素B(2),与硫酸软骨素A相似,但主要由L-艾杜糖醛酸组成,而不是D-葡萄糖醛酸。硫酸皮肤素和硫酸软骨素两者平均每个二糖单位含有一个硫酸基团。
Chondroitin and dermatan sulfates are families of structurally complex, sulfated, linear polysaccharides called glycosaminoglycans (GAGs) with alternating uronic acid and N-acetylated D-galactosamine residues [1](Scheme 1). Chondroitin sulfate A (1A) consists of unsulfated D-glucuronic acid 1--* 3 linked to N-acetylated, 4-sulfated D-galactosamine, which in turn is attached to the next D-glucuronic acid residue by a 1~ 4 linkage. Chondroitin sulfate C (1B) has a 6-sulfate group on the N-acetylated D-galactosamine in place of the 4-sulfate found in chondroitin sulfate A. Dermatan sulfate, also called chondroitin sulfate B (2), is similar to chondroitin sulfate A but instead of D-glucuronic acid it consists mainly of L-iduronic acid. Both dermatan and chondroitin sulfates contain, on the average, one sulfate group per disaccharide unit.