An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway

N-Protonation of amides is critical in numerous biological processes, including amide bonds proteolysis and protein folding as well as in organic synthesis as a method to activate amide bonds towards unconventional reactivity. A computational model enabling prediction of protonation at the amide bon...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-04, Vol.51 (29), p.6395-6398
Main Authors: Szostak, Roman, Aubé, Jeffrey, Szostak, Michal
Format: Article
Language:English
Subjects:
Amides
Amides - chemistry
Biology
Carbon - chemistry
Chemical bonds
Computation
Computer Simulation
Mathematical models
Models, Chemical
Nitrogen
Nitrogen - chemistry
Pathways
prediction
protein folding
proteolysis
Protonation
Protons
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Summary:N-Protonation of amides is critical in numerous biological processes, including amide bonds proteolysis and protein folding as well as in organic synthesis as a method to activate amide bonds towards unconventional reactivity. A computational model enabling prediction of protonation at the amide bond nitrogen atom along the C-N rotational pathway is reported. Notably, this study provides a blueprint for the rational design and application of amides with a controlled degree of rotation in synthetic chemistry and biology.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c5cc01034a