Revealing the structure of isolated peptides: IR-IR predissociation spectroscopy of protonated triglycine isomers

Voss, Jonathan M.; Fischer, Kaitlyn C.; Garand, Etienne

doi:10.1016/j.jms.2018.03.006

Title: Revealing the structure of isolated peptides: IR-IR predissociation spectroscopy of protonated triglycine isomers

Journal Article · 08 March 2018 · Journal of Molecular Spectroscopy

DOI: https://doi.org/10.1016/j.jms.2018.03.006 · OSTI ID:1434665

Voss, Jonathan M. ^[1]; Fischer, Kaitlyn C. ^[1];

^[1]

Univ. of Wisconsin, Madison, WI (United States)

Here, we report an isomer specific IR-IR double resonance study of the mass-selected protonated triglycine peptide. Comparison of experimental spectra with calculations reveals the presence of two isomers, with protonation occurring at either the terminal amine site or one of the amide oxygen sites. The amine protonated isomer identified in our experiment contains an atypical cis amide configuration as well as a more typical trans amide. The amide protonated peptide, on the other hand, contains two trans amide moieties. Both isomers are found to be the lowest energy structures for their respective protonation site, but it is unclear, from experiments and calculations, which one is the global minimum. The presence of both in our experiments likely points to kinetic trapping of a higher energy structure. Lastly, the observed frequencies of the NH and OH stretch vibrations are used to estimate the hydrogen-bond strengths present in each isomer, accounting for the relative stabilities of these structures.

View Accepted Manuscript (DOE)

View Accepted Manuscript (Publisher)

Cite

Export

Save

Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0010326

OSTI ID:: 1434665

Alternate ID(s):: OSTI ID: 1691641

Journal Information:: Journal of Molecular Spectroscopy, Vol. 347, Issue C; ISSN 0022-2852

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 20 works

Citation information provided by
Web of Science

References (35)

Protonation Sites and Conformations of Peptides of Glycine (Gly ₁₋₅ H ⁺ ) by IRMPD Spectroscopy Wu, Ronghu; McMahon, Terry B. The Journal of Physical Chemistry B, Vol. 113, Issue 25 https://doi.org/10.1021/jp811468q	journal	June 2009
Infrared Multiple Photon Dissociation Spectroscopy as Structural Confirmation for GlyGlyGlyH ⁺ and AlaAlaAlaH ⁺ in the Gas Phase. Evidence for Amide Oxygen as the Protonation Site Wu, Ronghu; McMahon, Terry B. Journal of the American Chemical Society, Vol. 129, Issue 37 https://doi.org/10.1021/ja0734492	journal	September 2007
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update Hunter, Edward P. L.; Lias, Sharon G. Journal of Physical and Chemical Reference Data, Vol. 27, Issue 3 https://doi.org/10.1063/1.556018	journal	May 1998
Thermodynamics and Reaction Mechanisms of Decomposition of the Simplest Protonated Tripeptide, Triglycine: A Guided Ion Beam and Computational Study Mookherjee, Abhigya; Van Stipdonk, Michael J.; Armentrout, P. B. Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 4 https://doi.org/10.1007/s13361-016-1590-y	journal	February 2017
Biomolecule Analysis by Ion Mobility Spectrometry Bohrer, Brian C.; Merenbloom, Samuel I.; Koeniger, Stormy L. Annual Review of Analytical Chemistry, Vol. 1, Issue 1 https://doi.org/10.1146/annurev.anchem.1.031207.113001	journal	July 2008
A Database of Alkaline-Earth-Coordinated Peptide Cross Sections: Insight into General Aspects of Structure Dilger, Jonathan M.; Valentine, Stephen J.; Glover, Matthew S. Journal of The American Society for Mass Spectrometry, Vol. 24, Issue 5 https://doi.org/10.1007/s13361-013-0579-z	journal	March 2013
Structural analysis of prion proteins by means of drift cell and traveling wave ion mobility mass spectrometry Hilton, Gillian R.; Thalassinos, Konstantinos; Grabenauer, Megan Journal of the American Society for Mass Spectrometry, Vol. 21, Issue 5 https://doi.org/10.1016/j.jasms.2010.01.017	journal	May 2010
Changes in protein structure monitored by use of gas-phase hydrogen/deuterium exchange Beeston, Helen S.; Ault, James R.; Pringle, Steven D. PROTEOMICS, Vol. 15, Issue 16 https://doi.org/10.1002/pmic.201400440	journal	March 2015
Gas-Phase H/D Exchange of Sodiated Glycine Oligomers with ND ₃ : Exchange Kinetics Do Not Reflect Parent Ion Structures Cox, Heather A.; Julian, Ryan R.; Lee, Sang-Won Journal of the American Chemical Society, Vol. 126, Issue 20 https://doi.org/10.1021/ja049834y	journal	May 2004
Conformational insight into multi-protein signaling assemblies by hydrogen–deuterium exchange mass spectrometry Harrison, Rane A.; Engen, John R. Current Opinion in Structural Biology, Vol. 41 https://doi.org/10.1016/j.sbi.2016.08.003	journal	December 2016
The beginning of a beautiful friendship: Cross-linking/mass spectrometry and modelling of proteins and multi-protein complexes Rappsilber, Juri Journal of Structural Biology, Vol. 173, Issue 3 https://doi.org/10.1016/j.jsb.2010.10.014	journal	March 2011
Chemical cross-linking and mass spectrometry to map three-dimensional protein structures and protein–protein interactions Sinz, Andrea Mass Spectrometry Reviews, Vol. 25, Issue 4 https://doi.org/10.1002/mas.20082	journal	January 2006
Electrospray ionization for mass spectrometry of large biomolecules Fenn, J.; Mann, M.; Meng, C. Science, Vol. 246, Issue 4926, p. 64-71 https://doi.org/10.1126/science.2675315	journal	October 1989
Electrospray ionization-principles and practice Fenn, John B.; Mann, Matthias; Meng, Chin Kai Mass Spectrometry Reviews, Vol. 9, Issue 1, p. 37-70 https://doi.org/10.1002/mas.1280090103	journal	January 1990
Charge-state resolved mid-infrared spectroscopy of a gas-phase protein Oomens, Jos; Polfer, Nick; Moore, David T. Physical Chemistry Chemical Physics, Vol. 7, Issue 7 https://doi.org/10.1039/b502322j	journal	January 2005
The structure of deprotonated tri-alanine and its a 3− fragment anion by IR spectroscopy Oomens, Jos; Steill, Jeffrey D. Journal of the American Society for Mass Spectrometry, Vol. 21, Issue 5 https://doi.org/10.1016/j.jasms.2010.01.004	journal	May 2010
Structural Characterization by IRMPD Spectroscopy and DFT Calculations of Deprotonated Phosphorylated Amino Acids in the Gas Phase Scuderi, D.; Correia, C. F.; Balaj, O. P. ChemPhysChem, Vol. 10, Issue 9-10 https://doi.org/10.1002/cphc.200800856	journal	July 2009
Infrared multiple photon dissociation spectroscopy of trapped ions Polfer, Nick C. Chemical Society Reviews, Vol. 40, Issue 5 https://doi.org/10.1039/c0cs00171f	journal	January 2011
Vibrational spectroscopy of bare and solvated ionic complexes of biological relevance Polfer, Nick C.; Oomens, Jos Mass Spectrometry Reviews, Vol. 28, Issue 3 https://doi.org/10.1002/mas.20215	journal	February 2009
Single-conformation infrared spectra of model peptides in the amide I and amide II regions: Experiment-based determination of local mode frequencies and inter-mode coupling Buchanan, Evan G.; James, William H.; Choi, Soo Hyuk The Journal of Chemical Physics, Vol. 137, Issue 9 https://doi.org/10.1063/1.4747507	journal	September 2012
Mixed 14/16 Helices in the Gas Phase: Conformation-Specific Spectroscopy of Z-(Gly) _n , n = 1, 3, 5 Dean, Jacob C.; Buchanan, Evan G.; Zwier, Timothy S. Journal of the American Chemical Society, Vol. 134, Issue 41 https://doi.org/10.1021/ja306652c	journal	October 2012
Exploring the Mechanism of IR-UV Double-Resonance for Quantitative Spectroscopy of Protonated Polypeptides and Proteins Nagornova, Natalia S.; Rizzo, Thomas R.; Boyarkin, Oleg V. Angewandte Chemie International Edition, Vol. 52, Issue 23 https://doi.org/10.1002/anie.201301656	journal	April 2013
Spectroscopic studies of cold, gas-phase biomolecular ions Rizzo, Thomas R.; Stearns, Jaime A.; Boyarkin, Oleg V. International Reviews in Physical Chemistry, Vol. 28, Issue 3 https://doi.org/10.1080/01442350903069931	journal	July 2009
Isomer-Specific IR–IR Double Resonance Spectroscopy of D ₂ -Tagged Protonated Dipeptides Prepared in a Cryogenic Ion Trap Leavitt, Christopher M.; Wolk, Arron B.; Fournier, Joseph A. The Journal of Physical Chemistry Letters, Vol. 3, Issue 9 https://doi.org/10.1021/jz3003074	journal	April 2012
Characterizing the Intramolecular H-bond and Secondary Structure in Methylated GlyGlyH+ with H2 Predissociation Spectroscopy Leavitt, Christopher M.; Wolk, Arron B.; Kamrath, Michael Z. Journal of The American Society for Mass Spectrometry, Vol. 22, Issue 11 https://doi.org/10.1007/s13361-011-0228-3	journal	August 2011
Intramolecular Hydrogen Bonding Motifs in Deprotonated Glycine Peptides by Cryogenic Ion Infrared Spectroscopy Marsh, Brett M.; Duffy, Erin M.; Soukup, Michael T. The Journal of Physical Chemistry A, Vol. 118, Issue 22 https://doi.org/10.1021/jp501936b	journal	May 2014
Vibrational spectroscopy of isolated copper( ii ) complexes with deprotonated triglycine and tetraglycine peptides Marsh, Brett M.; Zhou, Jia; Garand, Etienne RSC Advances, Vol. 5, Issue 3 https://doi.org/10.1039/C4RA09655J	journal	January 2015
A dual cryogenic ion trap spectrometer for the formation and characterization of solvated ionic clusters Marsh, Brett M.; Voss, Jonathan M.; Garand, Etienne The Journal of Chemical Physics, Vol. 143, Issue 20 https://doi.org/10.1063/1.4936360	journal	November 2015
Identification of the protonation site of gaseous triglycine: the cis-peptide bond conformation as the global minimum Li, Hongbao; Jiang, Jun; Luo, Yi Physical Chemistry Chemical Physics, Vol. 19, Issue 23 https://doi.org/10.1039/C7CP01997A	journal	January 2017
Cryogenic Ion Chemistry and Spectroscopy Wolk, Arron B.; Leavitt, Christopher M.; Garand, Etienne Accounts of Chemical Research, Vol. 47, Issue 1 https://doi.org/10.1021/ar400125a	journal	August 2013
Direct proportionality of the hydrogen bonding energy and the intensification of the stretching ν(XH) vibration in infrared spectra Iogansen, A. V. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 55, Issue 7-8 https://doi.org/10.1016/S1386-1425(98)00348-5	journal	July 1999
An empirical correlation between stretching vibration redshift and hydrogen bond length Rozenberg, Mark; Loewenschuss, Aharon; Marcus, Yizhak Physical Chemistry Chemical Physics, Vol. 2, Issue 12 https://doi.org/10.1039/b002216k	journal	January 2000
A correlation between the proton stretching vibration red shift and the hydrogen bond length in polycrystalline amino acids and peptides Rozenberg, Mark; Shoham, Gil; Reva, Igor Physical Chemistry Chemical Physics, Vol. 7, Issue 11 https://doi.org/10.1039/b503644e	journal	January 2005
Infrared studies of the less stable cis form of N-methylformmaide and N-methylacetamide in low-temperature nitrogen matrices and vibrational analyses of the trans and cis forms of these molecules Ataka, S.; Takeuchi, H.; Tasumi, M. Journal of Molecular Structure, Vol. 113 https://doi.org/10.1016/0022-2860(84)80140-4	journal	March 1984
Nmr studies of the molecular conformations in the linear oligopeptides H-( L -Ala) _n - L -Pro-OH: MOLECULAR CONFORMATIONS Grathwohl, Christoph; Wüthrich, Kurt Biopolymers, Vol. 15, Issue 10 https://doi.org/10.1002/bip.1976.360151013	journal	October 1976

Cited By (1)

The structures and properties of anionic tryptophan complexes Ieritano, Christian; Featherstone, Joshua; Carr, Patrick J. J. Physical Chemistry Chemical Physics, Vol. 20, Issue 41 https://doi.org/10.1039/c8cp04533j	journal	January 2018