Carbodiimide/NHS derivatization of COOH-terminated SAMs : activation or byproduct formation?

COOH-terminated self-assembled monolayers (SAMs) are widely used in biosensor technology to bind different amine-containing biomolecules. A covalent amide bond, however, can be achieved only if the carboxylic acids are activated. This activation process usually consists of forming an N-hydroxysuccin...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 30(2014), 16 vom: 29. Apr., Seite 4545-50
1. Verfasser: Palazon, Francisco (VerfasserIn)
Weitere Verfasser: Benavides, Cindy Montenegro, Léonard, Didier, Souteyrand, Éliane, Chevolot, Yann, Cloarec, Jean-Pierre
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2014
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Research Support, Non-U.S. Gov't Carbodiimides Carboxylic Acids Solvents
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520 |a COOH-terminated self-assembled monolayers (SAMs) are widely used in biosensor technology to bind different amine-containing biomolecules. A covalent amide bond, however, can be achieved only if the carboxylic acids are activated. This activation process usually consists of forming an N-hydroxysuccinimidyl ester (NHS-ester) by consecutively reacting carboxylic acids with a carbodiimide and NHS. Though many papers report using this method,1-8 the experimental conditions vary greatly between them and chemical characterization at this stage is often omitted. Evidence of an efficient activation is therefore rarely shown. Furthermore, recent publications9-11 have highlighted the complexity of this process, with the possible formation of different byproducts. In this paper, we have conducted a study on NHS activation under different conditions with chemical characterization by polarization-modulation infrared reflection-absorption spectroscopy (PM-IRRAS) and time-of-flight secondary ion mass spectroscopy (ToF-SIMS). Our results indicate that the nature of the solvent and carbodiimide and the reactant concentrations play crucial roles in activation kinetics and efficiency 
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650 4 |a Research Support, Non-U.S. Gov't 
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650 7 |a Carboxylic Acids  |2 NLM 
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700 1 |a Benavides, Cindy Montenegro  |e verfasserin  |4 aut 
700 1 |a Léonard, Didier  |e verfasserin  |4 aut 
700 1 |a Souteyrand, Éliane  |e verfasserin  |4 aut 
700 1 |a Chevolot, Yann  |e verfasserin  |4 aut 
700 1 |a Cloarec, Jean-Pierre  |e verfasserin  |4 aut 
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