Synthesis of azobenzenealkylmaleimide probes to photocontrol the enzyme activity of a bacterial histone deacetylase-like amidohydrolase

被引:13
|
作者
Horstmann, Benjamin [1 ]
Korbus, Michael [1 ]
Friedmann, Tatjana [1 ]
Wolff, Christiane [2 ]
Thiele, Christina Marie [2 ]
Meyer-Almes, Franz-Josef [1 ]
机构
[1] Univ Appl Sci Darmstadt, Dept Chem Engn & Biotechnol, D-64287 Darmstadt, Germany
[2] Tech Univ Darmstadt, Clemens Schopf Inst Organ Chem & Biochem, D-64287 Darmstadt, Germany
关键词
Deacetylation; External stimulus; Photochromism; Protein engineering; Photoswitch; Azobenzenes; Maleimides; Methylenemaleimideamide; Hofmann rearrangement; ANALOGS; ASSAY;
D O I
10.1016/j.bioorg.2014.10.004
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of azobenzenealkylmaleimides (AMDs) with different spacer length was synthesized and coupled via Michael-Addition to a specific mutant of a bacterial histone deacetylase-like amidohydrolase (HDAH). Michaelis-Menten parameters (V-max and K-m) were employed to characterize the effect of both, the spacer length and the configuration (cis vs. trans) of the attached azobenzene moiety, on the HDAH enzyme activity. The photoswitch behavior of the AMD/enzyme conjugate activity was clearly influenced by the AMD spacer length. This study highlights the importance of steric rearrangement of the photoswitch with respect to the active site and describes a strategy to optimize the photocontrol of HDAH. (C) 2014 Elsevier Inc. All rights reserved.
引用
收藏
页码:155 / 161
页数:7
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