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Updated: Jul 2, 2026

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
Published on: September 17, 2017
Enantiodiscrimination between an N-acetyl-L-cysteine SAM and proline: an in situ spectroscopic and computational
1Université de Neuchâtel, Institut de Chimie, Rue Emile-Argand 11, 2007 Neuchâtel (Switzerland).
Abstract:
A combination of attenuated total reflection infrared (ATR-IR) and modulation excitation spectroscopy (MES) is used to study the enantiodiscriminating interactions between proline and a chiral, self-assembled monolayer (SAM) of N-acetyl-L-cysteine on gold. The N-acetyl-L-cysteine SAM consists of a mixture of protonated and deprotonated molecules. Whereas both species are influenced by adsorbed proline, only the deprotonated molecules are involved in enantiodiscrimination. Density functional theory (DFT) calculations reveal that electrostatics dominates the interaction between the two molecules. By modulating the absolute configuration of proline over the chiral SAM, and a subsequent phase-sensitive detection of the periodically varying signals in the ATR-IR spectra, the small spectral differences between the diastereomeric complexes are spotted. The resulting difference spectrum is in qualitative agreement with the spectrum predicted by the DFT calculations.
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