Issue 6, 2022

Unleashing the shape of l-DOPA at last

Abstract

Herein, we report the first rotational study of neutral L-DOPA, an extensively used supramolecular synthon and an amino acid precursor of the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) using broadband and narrowband Fourier transform microwave spectroscopies coupled with a laser ablation vaporization system. The spectroscopic parameters derived from the analysis of the rotational spectrum conclusively identify the existence of four distinct conformers of L-DOPA in the supersonic jet, further rejecting the previously reported catechol ring-induced conformational restriction. The analysis of the 14N nuclear quadrupole coupling hyperfine structure further revealed the orientation of the N-bearing functional group, proving the existence of stabilizing N–H⋯π interactions for the observed structures.

Graphical abstract: Unleashing the shape of l-DOPA at last

Supplementary files

Article information

Article type
Paper
Submitted
05 Nov 2021
Accepted
08 Dec 2021
First published
09 Dec 2021

Phys. Chem. Chem. Phys., 2022,24, 3546-3554

Unleashing the shape of L-DOPA at last

M. Sanz-Novo, I. León, E. R. Alonso and J. L. Alonso, Phys. Chem. Chem. Phys., 2022, 24, 3546 DOI: 10.1039/D1CP05066D

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