Aspartame and Its Microhydrated Aggregates Revealed by Laser Spectroscopy: Water-Sweetener Interactions in the Gas Phase

Overview

Journal J Phys Chem A

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Aug 2

PMID 39091218

Authors

Paul Pinillos

Ander Camiruaga

Fernando Torres-Hernandez

Pierre Carcabal

Imanol Usabiaga

Jose A Fernandez

Rodrigo Martinez

Affiliations

Soon will be listed here.

Abstract

The popular sweetener, aspartame, is an agonist of the tongue's sweet taste receptor. How water molecules affect its conformation or which aspartame atoms are more prone to interact with solvent are helpful questions to understand its activity in different environments. Here, the combination of IR-UV spectroscopic techniques with computational simulations has been successfully applied to characterize aspartame·water clusters, showing that the addition of water molecules simplifies the conformational panorama of aspartame, favoring the formation of folded structures by interaction with the polar part of the molecule.

References

Camiruaga A, Goldsztejn G, Carcabal P . Isotopic dependence of intramolecular and intermolecular vibrational couplings in cooperative hydrogen bond networks: singly hydrated phenyl-α-D-mannopyranoside as a case study. Phys Chem Chem Phys. 2023; 25(17):12331-12341. DOI: 10.1039/d3cp00908d. View

Riboli E, Beland F, Lachenmeier D, Marques M, Phillips D, Schernhammer E . Carcinogenicity of aspartame, methyleugenol, and isoeugenol. Lancet Oncol. 2023; 24(8):848-850. DOI: 10.1016/S1470-2045(23)00341-8. View

Bagchi B . Water dynamics in the hydration layer around proteins and micelles. Chem Rev. 2005; 105(9):3197-219. DOI: 10.1021/cr020661+. View

Evangelista-Falcon W, Denhez C, Baena-Moncada A, Ponce-Vargas M . Revisiting the Sweet Taste Receptor T1R2-T1R3 through Molecular Dynamics Simulations Coupled with a Noncovalent Interactions Analysis. J Phys Chem B. 2023; 127(5):1110-1119. DOI: 10.1021/acs.jpcb.2c07180. View

Ramaekers R, Pajak J, Lambie B, Maes G . Neutral and zwitterionic glycine.H(2)O complexes: A theoretical and matrix-isolation Fourier transform infrared study. J Chem Phys. 2004; 120(9):4182-93. DOI: 10.1063/1.1643735. View

Alonso J, Pena I, Eugenia Sanz M, Vaquero V, Mata S, Cabezas C . Observation of dihydrated glycine. Chem Commun (Camb). 2013; 49(33):3443-5. DOI: 10.1039/c3cc40344k. View

Tian S, Sun X, Cao R, Yang J . Thermal stabilities of the microhydrated zwitterionic glycine: a kinetics and dynamics study. J Phys Chem A. 2008; 113(2):480-3. DOI: 10.1021/jp8092594. View

Bachrach S . Microsolvation of glycine: a DFT study. J Phys Chem A. 2008; 112(16):3722-30. DOI: 10.1021/jp711048c. View

Alonso J, Cocinero E, Lesarri A, Eugenia Sanz M, Lopez J . The glycine-water complex. Angew Chem Int Ed Engl. 2006; 45(21):3471-4. DOI: 10.1002/anie.200600342. View

10.

Blom M, Compagnon I, Polfer N, von Helden G, Meijer G, Suhai S . Stepwise solvation of an amino acid: the appearance of zwitterionic structures. J Phys Chem A. 2007; 111(31):7309-16. DOI: 10.1021/jp070211r. View

11.

Clarkson J, Baquero E, Shubert V, Myshakin E, Jordan K, Zwier T . Laser-initiated shuttling of a water molecule between H-bonding sites. Science. 2005; 307(5714):1443-6. DOI: 10.1126/science.1106977. View

12.

Biswal H, Loquais Y, Tardivel B, Gloaguen E, Mons M . Isolated monohydrates of a model peptide chain: effect of a first water molecule on the secondary structure of a capped phenylalanine. J Am Chem Soc. 2011; 133(11):3931-42. DOI: 10.1021/ja108643p. View

13.

Vaquero V, Eugenia Sanz M, Pena I, Mata S, Cabezas C, Lopez J . Alanine water complexes. J Phys Chem A. 2014; 118(14):2584-90. DOI: 10.1021/jp500862y. View

14.

de Vries M, Hobza P . Gas-phase spectroscopy of biomolecular building blocks. Annu Rev Phys Chem. 2007; 58:585-612. DOI: 10.1146/annurev.physchem.57.032905.104722. View

15.

Gloaguen E, Mons M, Schwing K, Gerhards M . Neutral Peptides in the Gas Phase: Conformation and Aggregation Issues. Chem Rev. 2020; 120(22):12490-12562. DOI: 10.1021/acs.chemrev.0c00168. View

16.

Gonzalez J, Usabiaga I, Arnaiz P, Leon I, Martinez R, Millan J . Competition between stacked and hydrogen bonded structures of cytosine aggregates. Phys Chem Chem Phys. 2017; 19(13):8826-8834. DOI: 10.1039/c6cp08476a. View

17.

Bannwarth C, Ehlert S, Grimme S . GFN2-xTB-An Accurate and Broadly Parametrized Self-Consistent Tight-Binding Quantum Chemical Method with Multipole Electrostatics and Density-Dependent Dispersion Contributions. J Chem Theory Comput. 2019; 15(3):1652-1671. DOI: 10.1021/acs.jctc.8b01176. View

18.

Espinoza C, Szczepanski J, Vala M, Polfer N . Glycine and its hydrated complexes: a matrix isolation infrared study. J Phys Chem A. 2010; 114(18):5919-27. DOI: 10.1021/jp1014115. View

19.

Oncak M, Lischka H, Slavicek P . Photostability and solvation: photodynamics of microsolvated zwitterionic glycine. Phys Chem Chem Phys. 2010; 12(19):4906-14. DOI: 10.1039/b925246k. View

20.

Kumar S, Mishra K, Singh S, Borish K, Dey S, Sarkar B . Observation of a weak intra-residue C5 hydrogen-bond in a dipeptide containing Gly-Pro sequence. J Chem Phys. 2019; 151(10):104309. DOI: 10.1063/1.5115040. View