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i,i + 1二硫代酰胺的电子相互作用:增强的荧光猝灭及n到π*相互作用的证据

Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions.

作者信息

Huang Yun, Ferrie John J, Chen Xing, Zhang Yitao, Szantai-Kis D Miklos, Chenoweth David M, Petersson E James

机构信息

Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, USA.

出版信息

Chem Commun (Camb). 2016 Jun 14;52(50):7798-801. doi: 10.1039/c6cc00105j.

DOI:10.1039/c6cc00105j
PMID:27229876
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4924517/
Abstract

Thioamide residues can be effective, minimally-perturbing fluorescence quenching probes for studying protein folding and proteolysis. In order to increase the level of quenching, we have here explored the use of adjacent dithioamides. We have found that they are more effective fluorescence quenchers, as expected, but we have also observed unexpected changes in the thioamide absorption spectra that may arise from n-to-π* interactions of the thiocarbonyls. We have made use of the increased quenching to improve the fluorescence turn-on of thioamide protease sensors.

摘要

硫代酰胺残基可以作为有效的、对荧光干扰最小的猝灭探针,用于研究蛋白质折叠和蛋白水解。为了提高猝灭水平,我们在此探索了相邻二硫代酰胺的用途。正如预期的那样,我们发现它们是更有效的荧光猝灭剂,但我们也观察到硫代酰胺吸收光谱中出现了意想不到的变化,这可能是由硫羰基的n到π*相互作用引起的。我们利用增强的猝灭作用来改善硫代酰胺蛋白酶传感器的荧光开启。

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本文引用的文献

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Efficient, Traceless Semi-Synthesis of α-Synuclein Labeled with a Fluorophore/Thioamide FRET Pair.高效、无痕的α-突触核蛋白半合成,该蛋白用荧光团/硫代酰胺荧光共振能量转移对标记。
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Effects of thionation and fluorination on cis-trans isomerization in tertiary amides: an investigation of N-alkylglycine (peptoid) rotamers.硫代和氟化对叔酰胺顺反异构化的影响:N-烷基甘氨酸(类肽)旋转异构体的研究
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Thioamide-based fluorescent protease sensors.基于硫酰胺的荧光蛋白酶传感器。
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