IR-IR Conformation Specific Spectroscopy of Na+(Glucose) Adducts

Voss, Jonathan M.; Kregel, Steven J.; Fischer, Kaitlyn C.; Garand, Etienne

doi:10.1007/s13361-017-1813-x

Title: IR-IR Conformation Specific Spectroscopy of Na⁺(Glucose) Adducts

Journal Article · Wed Sep 27 00:00:00 EDT 2017 · Journal of the American Society for Mass Spectrometry

DOI:https://doi.org/10.1007/s13361-017-1813-x· OSTI ID:1425956

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

^[1]

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

Here in this paper we report an IR-IR double resonance study of the structural landscape present in the Na⁺(glucose) complex. Our experimental approach involves minimal modifications to a typical IR predissociation setup, and can be carried out via ion-dip or isomer-burning methods, providing additional flexibility to suit different experimental needs. In the current study, the single-laser IR predissociation spectrum of Na⁺(glucose), which clearly indicates contributions from multiple structures, was experimentally disentangled to reveal the presence of three α-conformers and five β-conformers. Comparisons with calculations show that these eight conformations correspond to the lowest energy gas-phase structures with distinctive Na+ coordination.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: SC0010326; CHE-0840494

OSTI ID:: 1425956

Journal Information:: Journal of the American Society for Mass Spectrometry, Vol. 29, Issue 1; ISSN 1044-0305

Publisher:: American Society for Mass SpectrometryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 30 works

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References (40)

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
Gas phase vibrational spectroscopy of the protonated water pentamer: the role of isomers and nuclear quantum effects Fagiani, Matias R.; Knorke, Harald; Esser, Tim K. Physical Chemistry Chemical Physics, Vol. 18, Issue 38 https://doi.org/10.1039/C6CP05217G	journal	January 2016
Influence of alkali and alkaline earth metal salts on glucose conversion to 5-hydroxymethylfurfural in an aqueous system Combs, Elliot; Cinlar, Basak; Pagan-Torres, Yomaira Catalysis Communications, Vol. 30 https://doi.org/10.1016/j.catcom.2012.10.011	journal	January 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
Stretching frequency versus bond distance correlation of OD(H)⋯Y (Y  N, O, S, Se, Cl, Br, I) hydrogen bonds in solid hydrates Mikenda, W. Journal of Molecular Structure, Vol. 147, Issue 1-2 https://doi.org/10.1016/0022-2860(86)87054-5	journal	September 1986
Transition States for Glucopyranose Interconversion Lewis, Brett E.; Choytun, Nankishoresing; Schramm, Vern L. Journal of the American Chemical Society, Vol. 128, Issue 15 https://doi.org/10.1021/ja0573054	journal	April 2006
Factors controlling relative stability of anomers and hydroxymethyl conformers of glucopyranose Barrows, Susan E.; Storer, Joey W.; Cramer, Christopher J. Journal of Computational Chemistry, Vol. 19, Issue 10 https://doi.org/10.1002/(SICI)1096-987X(19980730)19:10<1111::AID-JCC1>3.0.CO;2-P	journal	July 1998
Dissolution of cellulose with ionic liquids and its application: a mini-review Zhu, Shengdong; Wu, Yuanxin; Chen, Qiming Green Chemistry, Vol. 8, Issue 4, p. 325-327 https://doi.org/10.1039/b601395c	journal	January 2006
Vibrational Spectroscopy of Microhydrated Conjugate Base Anions Asmis, Knut R.; Neumark, Daniel M. Accounts of Chemical Research, Vol. 45, Issue 1 https://doi.org/10.1021/ar2000748	journal	June 2011
A theoretical study of glucose mutarotation in aqueous solution Silva, Alexander M.; da Silva, Edilson C.; da Silva, Clarissa O. Carbohydrate Research, Vol. 341, Issue 8 https://doi.org/10.1016/j.carres.2006.02.035	journal	June 2006
Determination of Noncovalent Docking by Infrared Spectroscopy of Cold Gas-Phase Complexes Garand, E.; Kamrath, M. Z.; Jordan, P. A. Science, Vol. 335, Issue 6069 https://doi.org/10.1126/science.1214948	journal	January 2012
Conformationally resolved spectra of acetaminophen by UV-UV hole burning and IR dip spectroscopy in the gas phase Sohn, Woon Yong; Ishiuchi, Shun-ichi; Miyazaki, Mitsuhiko Phys. Chem. Chem. Phys., Vol. 15, Issue 3 https://doi.org/10.1039/C2CP43552G	journal	January 2013
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
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
How the Shape of an H-Bonded Network Controls Proton-Coupled Water Activation in HONO Formation Relph, R. A.; Guasco, T. L.; Elliott, B. M. Science, Vol. 327, Issue 5963 https://doi.org/10.1126/science.1177118	journal	January 2010
Sensing the anomeric effect in a solvent-free environment Cocinero, Emilio J.; Carcabal, Pierre; Vaden, Timothy D. Nature, Vol. 469, Issue 7328 https://doi.org/10.1038/nature09693	journal	January 2011
Disentangling the Contribution of Multiple Isomers to the Infrared Spectrum of the Protonated Water Heptamer Heine, Nadja; Fagiani, Matias R.; Asmis, Knut R. The Journal of Physical Chemistry Letters, Vol. 6, Issue 12 https://doi.org/10.1021/acs.jpclett.5b00879	journal	June 2015
Direct Measurement of Energy Thresholds to Conformational Isomerization in Tryptamine Dian, B. C. Science, Vol. 303, Issue 5661 https://doi.org/10.1126/science.1093731	journal	February 2004
Solvent-Driven Reductive Activation of Carbon Dioxide by Gold Anions Knurr, Benjamin J.; Weber, J. Mathias Journal of the American Chemical Society, Vol. 134, Issue 45 https://doi.org/10.1021/ja308991a	journal	November 2012
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
Hydration of guanidinium depends on its local environment Heiles, Sven; Cooper, Richard J.; DiTucci, Matthew J. Chemical Science, Vol. 6, Issue 6 https://doi.org/10.1039/C5SC00618J	journal	January 2015
BIRD (blackbody infrared radiative dissociation): Evolution, principles, and applications Dunbar, Robert C. Mass Spectrometry Reviews, Vol. 23, Issue 2 https://doi.org/10.1002/mas.10074	journal	January 2004
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
Oligosaccharide Analysis by Mass Spectrometry: A Review of Recent Developments Kailemia, Muchena J.; Ruhaak, L. Renee; Lebrilla, Carlito B. Analytical Chemistry, Vol. 86, Issue 1 https://doi.org/10.1021/ac403969n	journal	December 2013
Infrared studies of ionic clusters: The influence of Yuan T. Lee Lisy, James M. The Journal of Chemical Physics, Vol. 125, Issue 13 https://doi.org/10.1063/1.2338317	journal	October 2006
Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification Masellis, Chiara; Khanal, Neelam; Kamrath, Michael Z. Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 10 https://doi.org/10.1007/s13361-017-1728-6	journal	June 2017
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
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
Gas-phase infrared multiple photon dissociation spectroscopy of mass-selected molecular ions Oomens, Jos; Sartakov, Boris G.; Meijer, Gerard International Journal of Mass Spectrometry, Vol. 254, Issue 1-2 https://doi.org/10.1016/j.ijms.2006.05.009	journal	July 2006
Laser Probes of Conformational Isomerization in Flexible Molecules and Complexes Zwier, Timothy S. The Journal of Physical Chemistry A, Vol. 110, Issue 12 https://doi.org/10.1021/jp056390z	journal	March 2006
Isomer-Selective Detection of Hydrogen-Bond Vibrations in the Protonated Water Hexamer Heine, Nadja; Fagiani, Matias R.; Rossi, Mariana Journal of the American Chemical Society, Vol. 135, Issue 22 https://doi.org/10.1021/ja401359t	journal	May 2013
Characterization of the Oxygen Binding Motif in a Ruthenium Water Oxidation Catalyst by Vibrational Spectroscopy Duffy, Erin M.; Marsh, Brett M.; Voss, Jonathan M. Angewandte Chemie International Edition, Vol. 55, Issue 12 https://doi.org/10.1002/anie.201600350	journal	February 2016
Exo-anomeric effects on energies and geometries of different conformations of glucose and related systems in the gas phase and aqueous solution Cramer, Christopher J.; Truhlar, Donald G.; French, Alfred D. Carbohydrate Research, Vol. 298, Issue 1-2 https://doi.org/10.1016/S0008-6215(96)00297-2	journal	February 1997
IR-induced conformational isomerization of a helical peptide in a cold ion trap Seaiby, Caroline; Zabuga, Aleksandra V.; Svendsen, Annette The Journal of Chemical Physics, Vol. 144, Issue 1 https://doi.org/10.1063/1.4939528	journal	January 2016
Experimental and Theoretical Studies of Sodium Cation Interactions with d -Arabinose, Xylose, Glucose, and Galactose Heaton, A. L.; Armentrout, P. B. The Journal of Physical Chemistry A, Vol. 112, Issue 41 https://doi.org/10.1021/jp804113q	journal	October 2008
Probing the Hydrogen-Bonded Water Network at the Active Site of a Water Oxidation Catalyst: [Ru(bpy)(tpy)(H ₂ O)] ²⁺ ·(H ₂ O) _0–4 Duffy, Erin M.; Marsh, Brett M.; Garand, Etienne The Journal of Physical Chemistry A, Vol. 119, Issue 24 https://doi.org/10.1021/acs.jpca.5b04778	journal	May 2015
Cryogenic ion trap vibrational spectroscopy of hydrogen-bonded clusters relevant to atmospheric chemistry Heine, Nadja; Asmis, Knut R. International Reviews in Physical Chemistry, Vol. 34, Issue 1 https://doi.org/10.1080/0144235X.2014.979659	journal	December 2014
Kinetics of Glucose Mutarotation Assessed by an Equal-Amplitude Paired Polarized Heterodyne Polarimeter Lin, Chu-En; Yu, Chih-Jen; Chen, Chuan-Lin The Journal of Physical Chemistry A, Vol. 114, Issue 4 https://doi.org/10.1021/jp906523s	journal	February 2010
Isolating the spectra of cluster ion isomers using Ar-“tag” -mediated IR-IR double resonance within the vibrational manifolds: Application to NO[sub 2][sup −]⋅H[sub 2]O Elliott, Ben M.; Relph, Rachael A.; Roscioli, Joseph R. The Journal of Chemical Physics, Vol. 129, Issue 9 https://doi.org/10.1063/1.2966002	journal	January 2008
Correlation of O-H stretching frequencies and O-H…O hydrogen bond lengths in minerals Libowitzky, Engen Monatshefte für Chemie / Chemical Monthly, Vol. 130, Issue 8 https://doi.org/10.1007/BF03354882	journal	August 1999

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Interplay of H‐Bonds with Aromatics in Isolated Complexes Identifies Isomeric Carbohydrates Saparbaev, Erik; Kopysov, Vladimir; Yamaletdinov, Ruslan Angewandte Chemie, Vol. 131, Issue 22 https://doi.org/10.1002/ange.201902377	journal	April 2019
Interplay of H‐Bonds with Aromatics in Isolated Complexes Identifies Isomeric Carbohydrates Saparbaev, Erik; Kopysov, Vladimir; Yamaletdinov, Ruslan Angewandte Chemie International Edition, Vol. 58, Issue 22 https://doi.org/10.1002/anie.201902377	journal	May 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Glucose
Spectroscopy
Conformers
Metal ion

Title: IR-IR Conformation Specific Spectroscopy of Na+(Glucose) Adducts

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Title: IR-IR Conformation Specific Spectroscopy of Na⁺(Glucose) Adducts