对糖化物反应性的 conformational 影响:研究葡萄糖的高反应性 conformor
Ciaran McDonnell1, Oscar López, Paul Murphy
1Department of Chemistry, University College Dublin, Ireland.
Journal of the American Chemical Society
|September 30, 2004
概括
葡萄糖类的构造显著影响它们的反应性. 具体来说, (1)C(4) 形状显著增加了水解速率,支持了关于轴基团效应的理论.
科学领域:
- 碳水化合物化学 碳水化合物化学
- 有机化学 有机化学
- 生物物理化学 生物物理化学
背景情况:
- 糖化物构成对于理解碳水化合物的反应性至关重要.
- 建议使用 (1)C(4) 形状来增强反应性.
- 之前的研究表明,轴性基团影响了电子吸收.
研究的目的:
- 为了研究构造对糖化物反应性的影响.
- 为了使用3,6-无二糖化物作为反应性 (1)C(4) 葡萄糖构成的模型.
- 为了比较不同无水甘化物衍生物的反应性.
主要方法:
- 合成甲基3,6 - 无糖化物和相关的寡糖化物.
- 在受控条件下的水解速率研究.
- 对所研究的糖化物进行了合规分析.
主要成果:
- 甲基3,6-无水体-β-D-葡萄皮酸的水解速度比 (4) C(1) 甲基葡萄糖酸快200-400倍.
- 与甲基ββ-D-galactopyranoside相比,甲基3,6-无-β-D-galactopyranoside的反应性有所降低.
- 合成的寡糖在无水残留物上有选择性反应.
结论:
- 葡萄糖类的 (1) C (4) 构造使它们成为高度反应的物种.
- 这种增强的反应性支持了轴向OH组比赤道OH组少吸收电子的假设.
- 形态效应是糖化物水解速率的一个关键决定因素.
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