Document Detail

Synthesis of N epsilon-(7-diethylaminocoumarin-3-carboxyl)- and N epsilon-(7-methoxycoumarin-3-carboxyl)-L-Fmoc lysine as tools for protease cleavage detection by fluorescence.
MedLine Citation:
PMID:  15635646     Owner:  NLM     Status:  MEDLINE    
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.
Thomas Berthelot; Jean-Claude Talbot; Georges Laïn; Gérard Déleris; Laurent Latxague
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of peptide science : an official publication of the European Peptide Society     Volume:  11     ISSN:  1075-2617     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2005 Mar 
Date Detail:
Created Date:  2005-02-28     Completed Date:  2005-11-07     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  153-60     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2004 European Peptide Society and John Wiley & Sons, Ltd.
Groupe de Chimie Bio-Organique, Université Victor Segalen Bordeaux 2, France.
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MeSH Terms
Chromatography, High Pressure Liquid
Coumarins / chemical synthesis*,  chemistry,  metabolism*
Fluorescence Resonance Energy Transfer
Lysine / analogs & derivatives*,  chemical synthesis*,  chemistry,  metabolism*
Matrix Metalloproteinase 1 / metabolism*
Molecular Structure
Reg. No./Substance:
0/Coumarins; 0/N(epsilon)-(7-diethylaminocoumarin-3-carboxyl)-9-fluorenylmethoxycarbonyllysine; 0/N(epsilon)-(7-methoxycoumarin-3-carboxyl)-9-fluorenylmethoxycarbonyllysine; 56-87-1/Lysine; EC Metalloproteinase 1

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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