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

Abstract : 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 publications(9-11) 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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Submitted on : Monday, June 9, 2014 - 11:24:04 AM
Last modification on : Friday, October 26, 2018 - 10:37:14 AM

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Francisco Palazon, Cindy Montenegro Benavides, Didier Léonard, Eliane Souteyrand, Yann Chevolot, et al.. Carbodiimide/NHS derivatization of COOH-terminated SAMs: activation or byproduct formation?. Langmuir, American Chemical Society, 2014, 30 (16), pp.4545-4550. ⟨10.1021/la5004269⟩. ⟨hal-01003030⟩

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