Hydrogen Bond Strengthens Acceptor Group: The Curious Case of the C–H···O=C Bond
Abstract
:1. Introduction
2. Results and Discussion
- Monomer (single H-bond): The canonical α-helical H-bond between the carbonyl of valine 80 and the amide H of glycine 84 was mimicked by two N-methylacetamides.
- Dimer (two H-bonds): The inter-helical H-bonding system contained the canonical H-bond described above, with an additional noncanonical inter-helical hydrogen bond. The Cα-H of glycine 83 from the opposing helix is bonded to the same carbonyl of valine 80 that is also involved in the canonical hydrogen bond. This system was mimicked by two N-methylacetamides forming the canonical H-bond to which an acetylglycinemethylamide is hydrogen bonded.
3. Materials and Methods
3.1. Sample Preparation
3.1.1. Isotopic Label Synthesis
3.1.2. Peptide Synthesis and Purification
3.1.3. Peptide Reconstitution
3.2. FTIR Spectroscopy
3.3. Computational Details
3.3.1. Molecular Dynamic Simulations
3.3.2. Quantum Mechanical Calculations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Abbreviations
FTIR | Fourier transform infrared |
DFT | density functional theory |
MD | molecular dynamics |
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Basu, K.; Brielle, E.S.; Arkin, I.T. Hydrogen Bond Strengthens Acceptor Group: The Curious Case of the C–H···O=C Bond. Int. J. Mol. Sci. 2024, 25, 8606. https://doi.org/10.3390/ijms25168606
Basu K, Brielle ES, Arkin IT. Hydrogen Bond Strengthens Acceptor Group: The Curious Case of the C–H···O=C Bond. International Journal of Molecular Sciences. 2024; 25(16):8606. https://doi.org/10.3390/ijms25168606
Chicago/Turabian StyleBasu, Kingshuk, Esther S. Brielle, and Isaiah T. Arkin. 2024. "Hydrogen Bond Strengthens Acceptor Group: The Curious Case of the C–H···O=C Bond" International Journal of Molecular Sciences 25, no. 16: 8606. https://doi.org/10.3390/ijms25168606