Amide activation in ground and excited states

Ervin Kovács, B. Rózsa, Attila Csomos, I. Csizmadia, Zoltán Mucsi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Not all amide bonds are created equally. The purpose of the present paper is the reinterpretation of the amide group by means of two concepts: amidicity and carbonylicity. These concepts are meant to provide a new viewpoint in defining the stability and reactivity of amides. With the help of simple quantum-chemical calculations, practicing chemists can easily predict the outcome of a desired process. The main benefit of the concepts is their simplicity. They provide intuitive, but quasi-thermodynamic data, making them a practical rule of thumb for routine use. In the current paper we demonstrate the performance of our methods to describe the chemical character of an amide bond strength and the way of its activation methods. Examples include transamidation, acyl transfer and amide reductions. Also, the method is highly capable for simple interpretation of mechanisms for biological processes, such as protein splicing and drug mechanisms. Finally, we demonstrate how these methods can provide information about photo-activation of amides, through the examples of two caged neurotransmitter derivatives.

Original languageEnglish
Article number2859
JournalMolecules
Volume23
Issue number11
DOIs
Publication statusPublished - Nov 2 2018

Fingerprint

Excited states
Amides
Ground state
amides
Chemical activation
activation
ground state
excitation
Protein Splicing
neurotransmitters
Biological Phenomena
splicing
Thermodynamics
Neurotransmitter Agents
drugs
reactivity
Derivatives
proteins
thermodynamics
Pharmaceutical Preparations

Keywords

  • Activation
  • Acyl transfer
  • Amide
  • Amidicity
  • Carbonylicity
  • Excited state
  • Transamidation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Amide activation in ground and excited states. / Kovács, Ervin; Rózsa, B.; Csomos, Attila; Csizmadia, I.; Mucsi, Zoltán.

In: Molecules, Vol. 23, No. 11, 2859, 02.11.2018.

Research output: Contribution to journalArticle

Kovács, Ervin ; Rózsa, B. ; Csomos, Attila ; Csizmadia, I. ; Mucsi, Zoltán. / Amide activation in ground and excited states. In: Molecules. 2018 ; Vol. 23, No. 11.
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