Synthesis of N,N-dimethylaminopyrene-modified short peptides for chemical photocatalysis

Synthesis of N,N-dimethylaminopyrene-modified short peptides for chemical photocatalysis
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DOI:
10.1002/psc.2966
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发表时间:
2017-07-01
影响因子:
2.1
通讯作者:
Wagenknecht, Hans-Achim
Wagenknecht, Hans-Achim
中科院分区:
生物学4区
文献类型:
--
作者:
Hermann, Sergej;Wagenknecht, Hans-Achim

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报道了以1-N,N-二甲氨基芘为发色团的肽基光催化剂的合成及其在光催化降解中的应用。采用铜(I)催化的炔-叠氮环加成反应作为关键步骤,以定量产率制备不同短肽序列的肽-芘缀合物。光催化剂进行了评估,甲醇亲核加成到1,1-二苯基乙烯的产品与马尔可夫尼科夫型取向的短肽含有精氨酸作为底物结合位点,在水解过程中,因此,该反应是在没有添加剂的情况下进行的三乙胺,这是以前应用的电子穿梭。实现了底物的完全转化和加成产物的良好产率。版权所有(c)2017 European Peptide Society and John Wiley & Sons,Ltd.
The synthesis of peptide-based photocatalysts that use 1-N,N-dimethylaminopyrene as chromophore and their application in photocatalysis is reported. The copper(I)-catalyzed alkyne-azide cycloaddition was applied as key step to prepare the peptide-pyrene conjugates in quantitative yields for different short peptide sequences. The photocatalysts were evaluated for the nucleophilic addition of methanol to 1,1-diphenylethylenes to products with Markovnikov-type orientation The short peptides contain arginine as substrate binding site during photocatalysis, and thus, the reaction was performed without the additive triethylamine that was previously applied as electron shuttle. Full conversion of the substrate and good yields for the addition product were achieved. Copyright (c) 2017 European Peptide Society and John Wiley & Sons, Ltd.