Scope of amino acid recognition by cucurbit[8]uril

Scope of amino acid recognition by cucurbit[8]uril
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DOI:
10.1007/s10847-008-9464-y
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发表时间:
2008-12-01
影响因子:
2.3
通讯作者:
Urbach, A. R.
Urbach, A. R.
中科院分区:
化学4区
文献类型:
--
作者:
Rajgariah, P.;Urbach, A. R.

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本文研究了瓜环(Q8)及其与甲基紫精(MV)在纯水溶液中形成的1:1络合物对氨基酸的分子识别作用。众所周知,这些宿主结合芳香肽具有高亲和力和序列特异性,但以前的工作只集中在一小部分氨基酸上。为了阐明Q8和Q8中心点MV识别氨基酸的范围和局限性,用~1H核磁共振波谱和等温滴定量热法对20个基因编码的氨基酸进行了全面的研究。我们发现Q8和Q8中心点MV只与色氨酸、苯丙氨酸和酪氨酸有可测量的结合。这些结果表明,Q8和Q8中心点MV在所有遗传编码的氨基酸中都具有高度的选择性,因此有望开发涉及肽、蛋白质和蛋白质组的识别密集型应用。
This paper describes the molecular recognition of amino acids by cucurbit[8]uril (Q8) and by the 1:1 complex between Q8 and methyl viologen (MV) in purely aqueous solution. These hosts are known to bind aromatic peptides with high affinity and sequence specificity, but prior work has focused on only a small subset of amino acids. In an effort to elucidate the scope and limitations of amino acid recognition by Q8 and Q8 center dot MV, a comprehensive examination of the 20 genetically encoded amino acids was carried out by 1H NMR spectroscopy and isothermal titration calorimetry. We find that both Q8 and Q8 center dot MV bind measurably to only tryptophan, phenylalanine, and tyrosine. These results demonstrate that Q8 and Q8 center dot MV are highly selective in the context of all genetically encoded amino acids and are therefore promising for the development of recognition-intensive applications involving peptides, proteins, and proteomes.