探究碱金属与色氨酸侧链残基之间的π相互作用。
Probing alkali metal-pi interactions with the side chain residue of tryptophan.
作者信息
Hu Jiaxin, Barbour Leonard J, Gokel George W
机构信息
Program in Bioorganic Chemistry, Division of Bioorganic Chemistry, Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MO 63110, USA.
出版信息
Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5121-6. doi: 10.1073/pnas.082645599. Epub 2002 Apr 9.
Abstract
Feeble forces play a significant role in the organization of proteins. These include hydrogen bonding, hydrophobic interactions, salt bridge formation, and steric interactions. The alkali metal cation-pi interaction is a force of potentially profound importance but its consideration in biology has been limited by the lack of experimental evidence. Our previous studies of cation-pi interactions with Na(+) and K(+) involved the side arms of tryptophan (indole), tyrosine (phenol), and phenylalanine (benzene) as the arene donors. The receptor system possesses limiting steric constraints. In this report, we show that direct interactions between alkali metals and arenes occur at or within the van der Waals contact distance.
摘要
微弱作用力在蛋白质的结构形成中发挥着重要作用。这些作用力包括氢键、疏水相互作用、盐桥形成和空间相互作用。碱金属阳离子-π相互作用是一种可能具有深远意义的作用力，但由于缺乏实验证据，其在生物学中的研究一直受到限制。我们之前对Na(+)和K(+)阳离子-π相互作用的研究涉及色氨酸（吲哚）、酪氨酸（苯酚）和苯丙氨酸（苯）的侧链作为芳烃供体。受体系统存在有限的空间限制。在本报告中，我们表明碱金属与芳烃之间的直接相互作用发生在范德华接触距离处或其范围内。
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本文引用的文献
1
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Angew Chem Int Ed Engl. 1998 Dec 4;37(22):3152-3154. doi: 10.1002/(SICI)1521-3773(19981204)37:22<3152::AID-ANIE3152>3.0.CO;2-7.
2
Solid state evidence for pi-complexation of sodium cation by carbon-carbon double bonds.碳 - 碳双键对钠离子进行π络合的固态证据。
Chem Commun (Camb). 2001 Sep 21(18):1858-9. doi: 10.1039/b106589k.
3
The Cationminus signpi Interaction.阳离子减号π相互作用。
Chem Rev. 1997 Aug 5;97(5):1303-1324. doi: 10.1021/cr9603744.
4
Crystal Engineering in [(12C4)(2)Na][Cd(SCN)(3)]: First Example of an Anionic Cadmium Thiocyanate Coordination Solid with a Sandwich [(12C4)(2)Na](+) Cation as Spacer/Controller, Resulting in a Hexagonal Arrangement of Antiparallel Zigzag [Cd(SCN)(3)(-)](infinity) Chains.
Inorg Chem. 1998 Jul 13;37(14):3490-3496. doi: 10.1021/ic971487o.
5
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Inorg Chem. 1996 Dec 4;35(25):7264-7272. doi: 10.1021/ic960570t.
6
Solid-state evidence for pi-complexation of sodium and potassium cations by carbon-carbon triple bonds.
J Am Chem Soc. 2001 Sep 26;123(38):9486-7. doi: 10.1021/ja0112137.
7
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8
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