Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study.

Rodrigo Antonio Cormanich, Michael Buehl, Roberto Rittner

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10 Citations (Scopus)
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Abstract

The conformational behaviour of Ac-Ala-NHMe was studied for the compound in the gas-phase and in solution by theoretical calculations and experimental 1H NMR. The conformational preferences of this compound showed to be resultant from a complex interplay between the strengths of possible intramolecular hydrogen bonds, steric interactions, hyperconjugation, entropy effects and the overall dipole moments. The Ac-Ala-N(Me)2 derivative was used in order to simulate the effect of polar protic solvents in disrupting intramolecular hydrogen bonds involving the -NHMe group in Ac-Ala-NHMe.

Original languageEnglish
Pages (from-to)9206-9213
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume13
Issue number35
Early online date21 Jul 2015
DOIs
Publication statusPublished - 21 Sept 2015

Keywords

  • Dipeptide models

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