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Active transport of amino acids by a guanidiniocarbonyl-pyrrole receptor

机译：胍基羰基吡咯受体主动转运氨基酸

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摘要

Herein we report the synthesis and characterization of a transporter 9 for N-acetylated amino acids. Transporter 9 is a conjugate of a guanidiniocarbonyl pyrrole cation, one of the most efficient carboxylate binding motifs reported so far, and a hydrophobictris (dodecylbenzyl) group, which ensures solubility in organic solvents. In its protonated form, 9 binds N-acetylated amino acid carboxylates in wetorganic solvents with association constantsin the range of 10~4m~(-1) as estimated by extraction experiments. Aromatic amino acids are preferred due to additional cation-α-interactions of the amino acid side chain with the guanidiniocarbonyl pyrrole moiety. U-tube experiments established efficient transport across a bulk liquid chloroform phase with fluxes approaching 10~(-6) molm~(-2)s~(-1). In experiments with single substrates, the release rate of the amino acid from the receptor-substrate complex at the interface with the receiving phase is rate determining. In contrast to this, in competition experiments with several substrates, the therm-odynamic affinity to 9 becomes decisive. As 9 can only transport anions in its protonated form and has a pK_a value of approximately 7, pH-driven active transport of amino acids is also possible. Transport occurs as a symport of the amino acid carboxylate and a proton.
机译：在此，我们报道了N-乙酰化氨基酸转运蛋白9的合成和表征。转运蛋白9是胍基碘羰基吡咯阳离子（迄今为止报道的最有效的羧酸酯结合基序之一）和疏水性三（十二烷基苄基）基团的共轭物，可确保在有机溶剂中的溶解度。 9质子化形式的N-乙酰化氨基酸羧酸盐在湿有机溶剂中的结合常数在10〜4m〜（-1）范围内（通过萃取实验估算）。芳香族氨基酸是优选的，因为氨基酸侧链与胍基羰基吡咯部分的另外的阳离子-α-相互作用。 U型管实验建立了有效的跨体积液相氯仿相的传输，通量接近10〜（-6）molm〜（-2）s〜（-1）。在单一底物的实验中，氨基酸与受体-底物复合物在与接收相的界面处的释放速率决定了速率。与此相反，在具有几种底物的竞争实验中，对9的热动力学亲和力起决定性作用。因为9只能以质子化形式运输阴离子并且pK_a值约为7，所以pH驱动的氨基酸主动运输也是可能的。转运作为氨基酸羧酸盐和质子的同向发生。

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