Unleashing the shape of L-DOPA at last

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 spectrosco...

Full description

Saved in:
Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2022-02, Vol.24 (6), p.3546-3554
Main Authors: Sanz-Novo, Miguel, León, Iker, Alonso, Elena R, Alonso, José L
Format: Article
Language:English
Subjects:
Amino acids
Broadband
Catechol
Dihydroxyphenylalanine
Dopamine
Epinephrine
Fourier transforms
Functional groups
Hydrogen Bonding
Hyperfine structure
Laser ablation
Levodopa
Microwaves
Molecular Conformation
Narrowband
Neurotransmitters
Noradrenaline
Norepinephrine
Parameter identification
Quadrupole interaction
Quadrupoles
Rotational spectra
Spectrum Analysis
Vaporization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 N 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.
ISSN:1463-9076
1463-9084
DOI:10.1039/d1cp05066d