Choay J, Petitou M, Lormeau J C, Sinaÿ P, Casu B, Gatti G
Biochem Biophys Res Commun. 1983 Oct 31;116(2):492-9. doi: 10.1016/0006-291x(83)90550-8.
The structures of the tetrasaccharide (beta-D-glucuronic acid)1 leads to 4 (N-sulfate-3,6-di-0-sulfate-alpha-D-glucosamine)1 leads to 4(2-0-sulfate-alpha-L-iduronic acid)1 leads to 4(N-sulfate-6-0-sulfate-D-glucosamine) and of the pentasaccharide (N-sulfate-6-0-sulfate-alpha-D-glucosamine)1 leads to 4(beta-D-glucuronic acid)1 leads to 4(N-sulfate-3,6-di-0-sulfate-alpha-D-glucosamine)1 leads to 4(2-0-sulfate-alpha-L-iduronic acid)1 leads to 4(N-sulfate-6-0-sulfate-D-glucosamine), both prepared for the first time, by chemical synthesis from D-glucose and D-glucosamine, have been confirmed by nuclear magnetic resonance. The synthetic tetrasaccharide neither binds to AT-III nor induces anti-factor Xa activity enhancement of this inhibitor. In contrast, the synthetic pentasaccharide strongly binds to AT-III (Ka: 7.10(6)M-1) forming an equimolar complex and also enhances the AT-III inhibitory activity towards factor Xa. These results confirm that the synthetic pentasaccharide with the above structure corresponds to the actual minimal sequence required in heparin for binding to AT-III.
首次通过化学合成由D - 葡萄糖和D - 葡糖胺制备的四糖（β - D - 葡糖醛酸）1→4（N - 硫酸酯 - 3,6 - 二 - O - 硫酸酯 - α - D - 葡糖胺）1→4（2 - O - 硫酸酯 - α - L - 艾杜糖醛酸）1→4（N - 硫酸酯 - 6 - O - 硫酸酯 - D - 葡糖胺）和五糖（N - 硫酸酯 - 6 - O - 硫酸酯 - α - D - 葡糖胺）1→4（β - D - 葡糖醛酸）1→4（N - 硫酸酯 - 3,6 - 二 - O - 硫酸酯 - α - D - 葡糖胺）1→4（2 - O - 硫酸酯 - α - L - 艾杜糖醛酸）1→4（N - 硫酸酯 - 6 - O - 硫酸酯 - D - 葡糖胺）的结构已通过核磁共振得到证实。合成的四糖既不与抗凝血酶III结合，也不诱导该抑制剂的抗因子Xa活性增强。相比之下，合成的五糖与抗凝血酶III强烈结合（Ka：7.10(6)M - 1）形成等摩尔复合物，并且还增强了抗凝血酶III对因子Xa的抑制活性。这些结果证实，具有上述结构的合成五糖对应于肝素中与抗凝血酶III结合所需的实际最小序列。
