Molecular recognition of carbohydrates with acyclic pyridine-based receptors

Molecular recognition of carbohydrates with acyclic pyridine-based receptors
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DOI:
10.1021/jo048979k
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发表时间:
2004-10-29
影响因子:
3.6
通讯作者:
Boese, R
Boese, R
中科院分区:
化学2区
文献类型:
--
作者:
Mazik, M;Radunz, W;Boese, R

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评价了非环状吡啶类受体对单糖的识别能力。基于2,4,6-三甲基或2,4,6-三甲基框架的氨基吡啶受体在吡喃葡萄糖苷的识别中显示出高的β与α结合选择性。氨基吡啶受体在氮上的空间位阻较小,表现出高效率和反向选择性。2-氨基吡啶基团已被确立为单糖结合中的高效识别基团。影响受体1-15,不同的性质和数量的结合和间隔子单元用作建筑块的结合性能的因素进行了讨论。
The recognition capabilities of acyclic pyridine-based receptors toward monosaccharides were evaluated. Aminopyridine receptors based on the 2,4,6-trimethyl- or 2,4,6-triethylbenzene frame show high beta vs alpha binding selectivity in the recognition of glucopyranosides. Amidopyridine receptors, which are sterically less hindered at nitrogen, display high efficiency and an inverse selectivity. The 2-aminopyridine group has been established as a highly effective recognition group in the binding of monosaccharides. The factors influencing the binding properties of receptors 1-15, which differ in the nature and number of binding and spacer subunits used as the buildings blocks, are discussed.