Synthesis of Nε-(7-diethylaminocoumarin-3-carboxyl)- and Nε-(7-methoxycoumarin-3-carboxyl)-L-Fmoc lysine as tools for protease cleavage detection by fluorescence
Synthesis of Nε-(7-diethylaminocoumarin-3-carboxyl)- and Nε-(7-methoxycoumarin-3-carboxyl)-L-Fmoc lysine as tools for protease cleavage detection by fluorescence
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DOI：
10.1002/psc.608
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发表时间：
2005-03-01
影响因子：
2.1
通讯作者：
Latxague, L
中科院分区：
文献类型：
--
作者：
Berthelot, T;Talbot, JC;Latxague, L
制备了两个香豆素标记的赖氨酸作为荧光共振能量转移（FRET）对，用于肽切割检测。7-甲氧基和7-二乙胺香豆素-3-羧酸是根据已知方法的修改合成的。在溶液中通过羧酸香豆素衍生物的活性n -羟基琥珀酰亚胺酯在赖氨酸上进行标记，以获得高产率的目标化合物。随后，这些修饰的氨基酸被用于固相肽合成（SPPS），并通过FRET和/或淬火研究证明了它们在细胞外基质金属蛋白酶（MMP-1）活性测量中的潜在效用。版权所有(c) 2004欧洲肽协会和John Wiley T Sons， Ltd。
Two coumarin-labelled lysines were conveniently prepared as a fluorescence resonance energy transfer (FRET) pair for peptide cleavage detection. 7-Methoxy and 7-diethylamino coumarin-3-carboxylic acids were synthesized according to a modification of known procedures. Labelling at lysine was achieved in solution via the active N-hydroxysuccinimide ester of the carboxylic acid coumarin derivatives to give the target compounds in good yield. Subsequently, these modified amino acids were used in solid phase peptide synthesis (SPPS), and their potential utility in an extracellular matrix metalloprotease (MMP-1) activity measurement via FRET and/or quenching studies was demonstrated. Copyright (c) 2004 European Peptide Society and John Wiley T Sons, Ltd.