BORONIC ACIDS MEDIATE GLYCOSIDE TRANSPORT THROUGH A LIQUID ORGANIC MEMBRANE VIA REVERSIBLE FORMATION OF TRIGONAL BORONATE ESTERS
BORONIC ACIDS MEDIATE GLYCOSIDE TRANSPORT THROUGH A LIQUID ORGANIC MEMBRANE VIA REVERSIBLE FORMATION OF TRIGONAL BORONATE ESTERS
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DOI：
10.1021/jo00089a014
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发表时间：
1994-05-20
影响因子：
3.6
通讯作者：
SMITH, BD
中科院分区：
文献类型：
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作者：
MORIN, GT;PAUGAM, MF;SMITH, BD
研究了苯基硼酸和3-(1-金刚烷基甲酰胺)苯基硼酸在三辛基甲基氯化铵存在和不存在的情况下，对对硝基苯基β-D-吡喃葡萄糖苷(葡萄糖苷)、对硝基苯基β-D-半乳糖苷(半乳糖苷)、对硝基苯基β-D-甘露糖苷(甘露糖苷)和对硝基苯基β-D-木糖苷(木糖苷)的转运能力。在没有亲脂性铵离子的情况下，硼酸转运了大量的半乳糖苷，这表明转运是由三角硼酸酯的可逆形成所介导的。提取和传输实验作为pH的函数为这种传输机制提供了确凿的证据。观察到三方硼酸盐转运途径的二醇选择性顺序为顺式-α，伽马-二醇和顺式-α，β-二醇近似于反式-α，伽马-二醇，远大于反式-α，β-二醇。半乳糖苷的上行转运是通过在接收相中加入硼酸和在有机层中加入亲脂性的硼酸来实现的，这是一个由基团易位驱动的主动转运的功能仿生例子。
The ability of phenylboronic acid and 3-(1-adamantylcarboxamido)phenylboronic acid to mediate the transport of p-nitrophenyl beta-D-glucopyranoside (glucoside), p-nitrophenyl beta-D-galactopyranoside (galactoside), p-nitrophenyl beta-D-mannopyranoside (mannoside), and p-nitrophenyl beta-D-xylopyranoside (xyloside) through a liquid dichloroethane membrane in the presence and absence of trioctylmethylammonium chloride was determined. In the absence of the lipophilic ammonium cation, the boronic acids transported significant amounts of galactoside, suggesting that transport was mediated by reversible formation of a trigonal boronate ester. Extraction and transport experiments as a function of pH provided confirming evidence for this transport mechanism. The apparent order of diol selectivity for the trigonal boronate transport pathway was observed to be cis-alpha,gamma-diol>cis-alpha,beta-diol approximate to trans-alpha,gamma-diol much greater than trans-alpha,beta-diol. Uphill transport of galactoside was achieved by including boric acid in the receiving phase and lipophilic boronic acid in the organic layer, representing a functionally biomimetic example of active transport driven by group translocation.