Wu S J, Chun M W, Shin K H, Toida T, Park Y, Linhardt R J, Kim Y S
Natural Products Research Institute, Seoul National University, Korea.
Thromb Res. 1998 Dec 15;92(6):273-81. doi: 10.1016/s0049-3848(98)00146-7.
Acharan sulfate is a glycosaminoglycan prepared from the giant African snail, Achatina fulica. This polysaccharide has a repeating disaccharide structure of -->4)-2-deoxy-2-acetamido-alpha-D-glucopyranose (1-->4)-2-sulfo-alpha-L-idopyranosyluronic acid (1-->). Its structure is related to heparin and heparan sulfate but is distinctly different from all known members of these classes of glycosaminoglycans. Because of its structural similarities to heparin, chemically modified acharan sulfate was studied to understand the chemical structure effected its anticoagulant activity. After de-N-acetylation, acharan sulfate was N-sulfonated using either chlorosulfonic acid-pyridine or sulfur trioxide-trimethylamine complex. The sulfate level in these products ranged from 22 to 24%(w/w), significantly less than that of heparin at 36%. The molecular weight of both N-sulfoacharan sulfates were comparable with that of heparin. In vitro anticoagulant activity assays showed that N-sulfoacharan sulfate derivatives were moderately active for the inhibition of thrombin and neither product showed any measurable anti-factor Xa activity. The differences in the activities of N-sulfoacharan sulfates produced by these two methods are probably ascribable to a small level of concomitant O-sulfonation obtained when using chlorosulfonic acid-pyridine.
硫酸阿糖聚糖是一种从非洲大蜗牛（褐云玛瑙螺）中提取的糖胺聚糖。这种多糖具有重复的二糖结构，即→4)-2-脱氧-2-乙酰氨基-α-D-吡喃葡萄糖（1→4)-2-磺酸基-α-L-艾杜糖醛酸（1→）。其结构与肝素和硫酸乙酰肝素相关，但与这些糖胺聚糖类别的所有已知成员明显不同。由于其与肝素的结构相似性，对化学修饰的硫酸阿糖聚糖进行了研究，以了解化学结构对其抗凝活性的影响。脱N-乙酰化后，使用氯磺酸-吡啶或三氧化硫-三甲胺络合物对硫酸阿糖聚糖进行N-磺化。这些产物中的硫酸根含量在22%至24%（w/w）之间，明显低于肝素的36%。两种N-磺化硫酸阿糖聚糖的分子量与肝素相当。体外抗凝活性测定表明，N-磺化硫酸阿糖聚糖衍生物对凝血酶的抑制作用中等，且两种产物均未显示出任何可测量的抗Xa因子活性。这两种方法产生的N-磺化硫酸阿糖聚糖活性的差异可能归因于使用氯磺酸-吡啶时伴随产生的少量O-磺化。
