Self-assembled carbohydrate monolayers: Formation and surface selective molecular recognition
Self-assembled carbohydrate monolayers: Formation and surface selective molecular recognition
复制标题
DOI：
10.1021/la9802466
复制
发表时间：
1998-08-04
期刊：
影响因子：
3.9
通讯作者：
Russell, DA
中科院分区：
文献类型：
--
作者：
Revell, DJ;Knight, JR;Russell, DA
研究了具有代表性的硫代碳水化合物衍生物在金表面的自组装单分子膜(SAM)的形成，以构建模拟非键分子识别现象的人工碳水化合物支架。由(I)1-β-D-硫代葡萄糖(1)、(Ii)1-β-D-硫代葡萄糖四乙酸酯(2)和(Iii)2-硫代乙基α-D-甘露糖苷(3)制备了三种类型的碳水化合物自组装膜。随后，用反射吸收红外光谱(RAIRS)对每种SAM进行了光谱表征。在原位实现了酰化碳水化合物SAM的去保护，这表明可以在不破坏硫金键的情况下进行化学转化。对于甘露糖衍生物，其中的碳水化合物部分通过间隔单元-OCH2CH2SH从金表面分离，可以证明这种碳水化合物SAM能够选择性地与特定的碳水化合物结合蛋白，即刀豆蛋白A(ConA)相互作用。通过RAIRS和表面等离子体共振(SPR)测量，甘露糖衍生的SAM在ConA的溶液中产生了特异的结合作用。相反，当甘露糖SAM与L岩藻糖特异性凝集素紫草作用时，没有观察到这种结合。这些结果表明，特殊设计的碳水化合物衍生物的高度有序的自组装膜可以用来模拟自然细胞表面结构，并用于研究选择性分子识别相互作用。
The formation of self-assembled monolayers (SAMs) of representative thiocarbohydrate derivatives onto a gold surface has been investigated to build an artificial carbohydrate scaffold to mimic non-bonded molecular recognition phenomena. Three types of carbohydrate SAMs were formulated from (i) 1-beta-D-thioglucose (1), (ii) 1-beta-D-thioglucose tetraacetate (2), and (iii) 2-mercaptoethyl alpha-D-mannopyranoside (3). Subsequently, each SAM was spectroscopically characterized by reflection-absorption infrared spectroscopy (RAIRS). Deprotection of the acylated carbohydrate SAM was achieved in situ, indicating that chemical transformation may be performed without disruption of the sulfur-gold bond. With the mannose derivative, in which the carbohydrate moiety was separated from the gold surface by the spacer unit -OCH2CH2SH, it was possible to demonstrate that such a carbohydrate SAM was able to interact selectively with a specific carbohydrate binding protein, i.e., concanavalin A (Con A). Exposure of the mannose derived SAM to a solution of Con A led to a specific binding interaction as measured by RAIRS and surface plasmon resonance (SPR). In contrast, on exposure of the mannose SAM to the L-fucose-specific lectin tetragonolobus purpureas, no such binding was observed. These results suggest that highly ordered SAMs of specifically designed carbohydrate derivatives can be formulated to mimic natural cell surface structures and used to study selective molecular recognition interactions.