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The effect of N-methylation on the conformational landscape of alanine: the case of N-methyl-L-alanine

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Abstract

The non-proteinogenic amino acid N-methyl-L-alanine has been brought into the gas phase using laser ablation techniques and studied by high resolution chirped pulse and molecular-beam Fourier transform microwave spectroscopies coupled to supersonic expansion. Four conformers showing the three types of hydrogen bond interactions I (NH⋯O[double bond, length as m-dash]C), II (OH⋯N) and III (N–H⋯O–H) have been unambiguously identified, based on the comparison of the experimental rotational and 14N nuclear quadrupole constants with the calculated ab initio values. The observation of a type III conformer evidences the role of methyl groups in both sides to impose the steric hindrance, precluding the relaxation from type III to type I conformers and explains the responsibility for the unique conformational landscape observed in the case of NMA.

Graphical abstract: The effect of N-methylation on the conformational landscape of alanine: the case of N-methyl-l-alanine

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Publication details

The article was received on 26 Sep 2018, accepted on 07 Nov 2018 and first published on 08 Nov 2018


Article type: Paper
DOI: 10.1039/C8CP06043F
Citation: Phys. Chem. Chem. Phys., 2018, Advance Article
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    The effect of N-methylation on the conformational landscape of alanine: the case of N-methyl-L-alanine

    E. M. Neeman, I. León, E. R. Alonso, L. Kolesniková, S. Mata and J. L. Alonso, Phys. Chem. Chem. Phys., 2018, Advance Article , DOI: 10.1039/C8CP06043F

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