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间苯二胺和对苯二胺作为增强型肟连接催化剂在蛋白质标记、聚乙二醇化、固定化及释放中的应用。

Application of meta- and para-Phenylenediamine as Enhanced Oxime Ligation Catalysts for Protein Labeling, PEGylation, Immobilization, and Release.

作者信息

Mahmoodi Mohammad M, Rashidian Mohammad, Zhang Yi, Distefano Mark D

机构信息

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota.

出版信息

Curr Protoc Protein Sci. 2015 Feb 2;79:15.4.1-15.4.28. doi: 10.1002/0471140864.ps1504s79.

DOI:10.1002/0471140864.ps1504s79
PMID:25640893
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4357315/
Abstract

Meta- and para-phenylenediamines have recently been shown to catalyze oxime and hydrazone ligation reactions at rates much faster than aniline, a commonly used catalyst. Here, we demonstrate how these new catalysts can be used in a generally applicable procedure for fluorescent labeling, PEGylation, immobilization, and release of aldehyde- and ketone- functionalized proteins. The chemical orthogonality of phenylenediamine-catalyzed oxime ligation versus copper-catalyzed click reaction has also been harnessed for simultaneous dual labeling of bifunctional proteins containing both aldehyde and alkyne groups in high yield.

摘要

间苯二胺和对苯二胺最近被证明能够催化肟和腙连接反应,其速率比常用催化剂苯胺快得多。在此,我们展示了如何将这些新型催化剂用于醛基和酮基功能化蛋白质的荧光标记、聚乙二醇化、固定化及释放的通用方法中。苯二胺催化的肟连接反应与铜催化的点击反应的化学正交性也已被用于高产率地同时对含有醛基和炔基的双功能蛋白质进行双重标记。

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本文引用的文献

1
High-yielding and photolabile approaches to the covalent attachment of biomolecules to surfaces via hydrazone chemistry.通过腙化学将生物分子共价连接到表面的高产且光不稳定的方法。
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Finding the right (bioorthogonal) chemistry.找到合适的(生物正交)化学物质。
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Enhanced catalysis of oxime-based bioconjugations by substituted anilines.取代苯胺对肟基生物共轭反应的催化作用增强。
Bioconjug Chem. 2014 Jan 15;25(1):93-101. doi: 10.1021/bc400380f. Epub 2013 Dec 17.
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Chemoenzymatic site-specific reversible immobilization and labeling of proteins from crude cellular extract without prior purification using oxime and hydrazine ligation.利用肟和肼连接反应,无需预先纯化,对粗细胞提取物中的蛋白质进行化学酶法位点特异性可逆固定和标记。
Curr Protoc Chem Biol. 2013;5(2):89-109. doi: 10.1002/9780470559277.ch120247.
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A general method for fluorescent labeling of the N-termini of lanthipeptides and its application to visualize their cellular localization.一种用于荧光标记细菌素 N 端的通用方法及其在细胞定位可视化中的应用。
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8
A highly efficient catalyst for oxime ligation and hydrazone-oxime exchange suitable for bioconjugation.一种高效的肟连接和腙肟交换催化剂,适用于生物偶联。
Bioconjug Chem. 2013 Mar 20;24(3):333-42. doi: 10.1021/bc3004167. Epub 2013 Mar 6.
9
Site-specific chemical protein conjugation using genetically encoded aldehyde tags.利用基因编码的醛标签进行位点特异性化学蛋白质偶联。
Nat Protoc. 2012 May 10;7(6):1052-67. doi: 10.1038/nprot.2012.045.
10
Chemoenzymatic reversible immobilization and labeling of proteins without prior purification.无预先纯化的化学酶促可逆固定化和蛋白质标记。
J Am Chem Soc. 2012 May 23;134(20):8455-67. doi: 10.1021/ja211308s. Epub 2012 May 8.