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荧光氨基酸二甲基氨基吖啶基丙氨酸的合成与表征

Synthesis and characterization of fluorescent amino acid dimethylaminoacridonylalanine.

作者信息

Jones Chloe M, Petersson George A, Petersson E James

机构信息

Department of Chemistry; University of Pennsylvania; 231 South 34th Street; Philadelphia, Pennsylvania 19104-6323, USA.

Biochemistry and Molecular Biophysics Graduate Group; University of Pennsylvania; 3700 Hamilton Walk, Philadelphia, PA 19104, USA.

出版信息

ARKIVOC. 2021;2021:97-109. doi: 10.24820/ark.5550190.p011.498. Epub 2021 Apr 5.

DOI:10.24820/ark.5550190.p011.498
PMID:33967634
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8104435/
Abstract

Fluorescent amino acids are powerful biophysical tools as they can be used in structural or imaging studies of a given protein without significantly perturbing its native fold or function. Here, we have synthesized and characterized 7-(dimethylamino)acridon-2-ylalanine (Dad), a red-shifted derivative of the genetically-incorporable amino acid, acridon-2-ylalanine. Alkylation increases the quantum yield and fluorescence lifetime of Dad relative to a previously published amino acid, 7-aminoacridon-2-ylalanine (Aad). These properties of Dad make it a potentially valuable protein label, and we have performed initial testing of its ability to be genetically incorporated using an evolved aminoacyl tRNA synthetase.

摘要

荧光氨基酸是强大的生物物理工具,因为它们可用于特定蛋白质的结构或成像研究,而不会显著干扰其天然折叠或功能。在此,我们合成并表征了7-(二甲基氨基)吖啶-2-基丙氨酸(Dad),它是可遗传掺入的氨基酸吖啶-2-基丙氨酸的红移衍生物。与之前报道的氨基酸7-氨基吖啶-2-基丙氨酸(Aad)相比,烷基化提高了Dad的量子产率和荧光寿命。Dad的这些特性使其成为一种潜在有价值的蛋白质标记物,并且我们已经使用进化的氨酰-tRNA合成酶对其进行遗传掺入能力的初步测试。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/b39b21375f6a/nihms-1697208-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/7b627605ae0a/nihms-1697208-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/789bc95ce0cf/nihms-1697208-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/0ffa727506aa/nihms-1697208-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/d3e0e880718b/nihms-1697208-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/b4da844d7738/nihms-1697208-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/b39b21375f6a/nihms-1697208-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/7b627605ae0a/nihms-1697208-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/789bc95ce0cf/nihms-1697208-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/0ffa727506aa/nihms-1697208-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/d3e0e880718b/nihms-1697208-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/b4da844d7738/nihms-1697208-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ade0/8104435/b39b21375f6a/nihms-1697208-f0007.jpg

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Rational design of small molecule fluorescent probes for biological applications.用于生物应用的小分子荧光探针的合理设计。
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Protein labeling for FRET with methoxycoumarin and acridonylalanine.用于荧光共振能量转移的甲氧基香豆素和吖啶基丙氨酸蛋白质标记
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The Kinetic and Molecular Basis for the Interaction of LexA and Activated RecA Revealed by a Fluorescent Amino Acid Probe.LexA 与活化 RecA 相互作用的动力学和分子基础通过荧光氨基酸探针揭示。
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