Observation of Conformational Simplification upon N-methylation on Amino Acid Iodide Clusters

Cao, Wenjin; Zhang, Hanhui; Yuan, Qinqin; Zhou, Xiaoguo; Kass, Steven R.; Wang, Xue-Bin

doi:10.1021/acs.jpclett.1c00125

Title: Observation of Conformational Simplification upon N-methylation on Amino Acid Iodide Clusters

Journal Article · Thu Mar 25 00:00:00 EDT 2021 · Journal of Physical Chemistry Letters

DOI:https://doi.org/10.1021/acs.jpclett.1c00125· OSTI ID:1788168

Cao, Wenjin ^[1]; Zhang, Hanhui ^[2]; Yuan, Qinqin ^[1]; Zhou, Xiaoguo ^[3]; Kass, Steven R. ^[4];

^[1]

BATTELLE (PACIFIC NW LAB)
UNIVERSITY PROGRAMS
Hefei University of Technology
University of Minnesota

This work reports a surprising observation that methylation of glycine-iodide cluster leads to less conformations and spectroscopic simplicity. We used cryogenic “iodide-tagging” negative ion photoelectron spectroscopy (NIPES) to probe specific binding sites of three N-methylated glycine derivatives, i.e., N-methylglycine (sarcosine, Sar), N,N-dimethylglycine (Dmg), and N,N,N-trimethylglycine (glycine betaine, Bet). NIPES reveals a progressive spectral simplification of the iodide clusters with increasing methylation due to the presence of fewer contributing structures, a reduction in the number of NH and OH hydrogen bond donating sites, and an increase in the basicity of the amine. Low energy conformers and tautomers of each cluster are computationally identified, and those observed in the experiments are assigned based on excellent agreement between the NIPE spectra and theoretical simulations. Clusters with zwitterionic structures for Gly, Sar, and Dmg are found to be less stable than their canonical forms and do not contribute to the observed spectra. This work demonstrates the power of “iodide-tagging” NIPES in probing conformational and tautomeric structures of amino acid-iodide clusters and provides a molecular level understanding on the effect of methyl substitution on the active binding sites of amino acids.

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Research Organization:: Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1788168

Report Number(s):: PNNL-SA-159020

Journal Information:: Journal of Physical Chemistry Letters, Vol. 12, Issue 11

Country of Publication:: United States

Language:: English

References (50)

Amino acid neurotransmitters and their pathways in the mammalian central nervous system Fagg, G. E.; Foster, A. C. Neuroscience, Vol. 9, Issue 4 https://doi.org/10.1016/0306-4522(83)90263-4	journal	August 1983
Effect of solvation on the acid/base properties of glycine Locke, Michael J.; McIver, Robert T. Journal of the American Chemical Society, Vol. 105, Issue 13 https://doi.org/10.1021/ja00351a017	journal	June 1983
Zwitterion formation in hydrated amino acid, dipole bound anions: How many water molecules are required? Xu, Shoujun; Nilles, J. Michael; Bowen, Kit H. The Journal of Chemical Physics, Vol. 119, Issue 20 https://doi.org/10.1063/1.1620501	journal	November 2003
One Water Molecule Stabilizes the Cationized Arginine Zwitterion Bush, Matthew F.; Prell, James S.; Saykally, Richard J. Journal of the American Chemical Society, Vol. 129, Issue 44 https://doi.org/10.1021/ja073796b	journal	November 2007
Infrared Spectroscopy of Cationized Arginine in the Gas Phase: Direct Evidence for the Transition from Nonzwitterionic to Zwitterionic Structure Bush, Matthew F.; O'Brien, Jeremy T.; Prell, James S. Journal of the American Chemical Society, Vol. 129, Issue 6 https://doi.org/10.1021/ja066335j	journal	February 2007
Effects of Alkaline Earth Metal Ion Complexation on Amino Acid Zwitterion Stability: Results from Infrared Action Spectroscopy Bush, Matthew F.; Oomens, Jos; Saykally, Richard J. Journal of the American Chemical Society, Vol. 130, Issue 20 https://doi.org/10.1021/ja711343q	journal	April 2008
Proton Affinity and Zwitterion Stability: New Results from Infrared Spectroscopy and Theory of Cationized Lysine and Analogues in the Gas Phase Bush, Matthew F.; Oomens, Jos; Williams, Evan R. The Journal of Physical Chemistry A, Vol. 113, Issue 2 https://doi.org/10.1021/jp807470p	journal	December 2008
Vibrational Signature of Charge Solvation vs Salt Bridge Isomers of Sodiated Amino Acids in the Gas Phase Kapota, Catherine; Lemaire, Joël; Maître, Philippe Journal of the American Chemical Society, Vol. 126, Issue 6 https://doi.org/10.1021/ja036932v	journal	February 2004
Conformation Switching in Gas-Phase Complexes of Histidine with Alkaline Earth Ions Dunbar, Robert C.; Hopkinson, Alan C.; Oomens, Jos The Journal of Physical Chemistry B, Vol. 113, Issue 30 https://doi.org/10.1021/jp903064w	journal	July 2009
Infrared Multiphoton Dissociation Spectroscopy of Cationized Serine: Effects of Alkali-Metal Cation Size on Gas-Phase Conformation Armentrout, P. B.; Rodgers, M. T.; Oomens, J. The Journal of Physical Chemistry A, Vol. 112, Issue 11 https://doi.org/10.1021/jp710885a	journal	February 2008
Infrared Spectroscopy of Phenylalanine Ag(I) and Zn(II) Complexes in the Gas Phase Polfer, Nick C.; Oomens, Jos; Moore, David T. Journal of the American Chemical Society, Vol. 128, Issue 2 https://doi.org/10.1021/ja0549291	journal	January 2006
Zn ²⁺ and Cd ²⁺ cationized serine complexes: infrared multiple photon dissociation spectroscopy and density functional theory investigations Coates, Rebecca A.; Boles, Georgia C.; McNary, Christopher P. Physical Chemistry Chemical Physics, Vol. 18, Issue 32 https://doi.org/10.1039/C6CP03805K	journal	January 2016
Zinc and Cadmium Complexation of l -Threonine: An Infrared Multiple Photon Dissociation Spectroscopy and Theoretical Study Boles, Georgia C.; Hightower, Randy L.; Berden, Giel The Journal of Physical Chemistry B, Vol. 123, Issue 44 https://doi.org/10.1021/acs.jpcb.9b08184	journal	October 2019
Binding Energies of Water to Sodiated Valine and Structural Isomers in the Gas Phase: The Effect of Proton Affinity on Zwitterion Stability Lemoff, Andrew S.; Bush, Matthew F.; Williams, Evan R. Journal of the American Chemical Society, Vol. 125, Issue 44 https://doi.org/10.1021/ja034544n	journal	November 2003
Effects of anions on the zwitterion stability of Glu, His and Arg investigated by IRMPD spectroscopy and theory O’Brien, Jeremy T.; Prell, James S.; Berden, Giel International Journal of Mass Spectrometry, Vol. 297, Issue 1-3 https://doi.org/10.1016/j.ijms.2010.07.003	journal	November 2010
Zwitterion vs Neutral Structures of Amino Acids Stabilized by a Negatively Charged Site: Infrared Photodissociation and Computations of Proline–Chloride Anion Schmidt, Jacob; Kass, Steven R. The Journal of Physical Chemistry A, Vol. 117, Issue 23 https://doi.org/10.1021/jp402267c	journal	May 2013
Assessing the impact of anion–π effects on phenylalanine ion structures using IRMPD spectroscopy Burt, Michael; Wilson, Kathleen; Marta, Rick Phys. Chem. Chem. Phys., Vol. 16, Issue 44 https://doi.org/10.1039/C4CP03776F	journal	January 2014
Complexation of halide ions to tyrosine: role of non-covalent interactions evidenced by IRMPD spectroscopy Corinti, Davide; Gregori, Barbara; Guidoni, Leonardo Physical Chemistry Chemical Physics, Vol. 20, Issue 6 https://doi.org/10.1039/C7CP06657K	journal	January 2018
Collision-Induced Dissociation of Halide Ion–Arginine Complexes: Evidence for Anion-Induced Zwitterion Formation in Gas-Phase Arginine Milner, Edward M.; Nix, Michael G. D.; Dessent, Caroline E. H. The Journal of Physical Chemistry A, Vol. 116, Issue 2 https://doi.org/10.1021/jp208183p	journal	January 2012
Performance of M06, M06-2X, and M06-HF Density Functionals for Conformationally Flexible Anionic Clusters: M06 Functionals Perform Better than B3LYP for a Model System with Dispersion and Ionic Hydrogen-Bonding Interactions Walker, Martin; Harvey, Andrew J. A.; Sen, Ananya The Journal of Physical Chemistry A, Vol. 117, Issue 47 https://doi.org/10.1021/jp408166m	journal	November 2013
On the Stability of Amino Acid Zwitterions in the Gas Phase: The Influence of Derivatization, Proton Affinity, and Alkali Ion Addition Wyttenbach, Thomas; Witt, Matthias; Bowers, Michael T. Journal of the American Chemical Society, Vol. 122, Issue 14 https://doi.org/10.1021/ja992546v	journal	March 2000
Cryogenic “Iodide-Tagging” Photoelectron Spectroscopy: A Sensitive Probe for Specific Binding Sites of Amino Acids Zhang, Hanhui; Cao, Wenjin; Yuan, Qinqin The Journal of Physical Chemistry Letters, Vol. 11, Issue 11 https://doi.org/10.1021/acs.jpclett.0c01099	journal	May 2020
Tetraalkylammonium Salts as Hydrogen-Bonding Catalysts Shirakawa, Seiji; Liu, Shiyao; Kaneko, Shiho Angewandte Chemie International Edition, Vol. 54, Issue 52 https://doi.org/10.1002/anie.201508659	journal	November 2015
Structural considerations for charge‐enhanced Brønsted acid catalysts Payne, Curtis; Kass, Steven R. Journal of Physical Organic Chemistry, Vol. 33, Issue 8 https://doi.org/10.1002/poc.4069	journal	March 2020
A general method for site-specific incorporation of unnatural amino acids into proteins Noren, C.; Anthony-Cahill, S.; Griffith, M. Science, Vol. 244, Issue 4901 https://doi.org/10.1126/science.2649980	journal	April 1989
Expanding the Genetic Code of Escherichia coli Wang, L.; Brock, A.; Herberich, B. Science, Vol. 292, Issue 5516, p. 498-500 https://doi.org/10.1126/science.1060077	journal	April 2001
Incorporation of Nonnatural Amino Acids Into Proteins Hendrickson, Tamara L.; Crécy-Lagard, Valérie de; Schimmel, Paul Annual Review of Biochemistry, Vol. 73, Issue 1 https://doi.org/10.1146/annurev.biochem.73.012803.092429	journal	June 2004
Encoding multiple unnatural amino acids via evolution of a quadruplet-decoding ribosome Neumann, Heinz; Wang, Kaihang; Davis, Lloyd Nature, Vol. 464, Issue 7287 https://doi.org/10.1038/nature08817	journal	February 2010
Synthesis of site-specific antibody-drug conjugates using unnatural amino acids Axup, J. Y.; Bajjuri, K. M.; Ritland, M. Proceedings of the National Academy of Sciences, Vol. 109, Issue 40 https://doi.org/10.1073/pnas.1211023109	journal	September 2012
Production of Site-Specific Antibody–Drug Conjugates Using Optimized Non-Natural Amino Acids in a Cell-Free Expression System Zimmerman, Erik S.; Heibeck, Tyler H.; Gill, Avinash Bioconjugate Chemistry, Vol. 25, Issue 2 https://doi.org/10.1021/bc400490z	journal	January 2014
RF1 attenuation enables efficient non-natural amino acid incorporation for production of homogeneous antibody drug conjugates Yin, Gang; Stephenson, Heather T.; Yang, Junhao Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-017-03192-z	journal	June 2017
Unnatural Amino Acid Mutagenesis of Green Fluorescent Protein Wang, Lei; Xie, Jianming; Deniz, Ashok A. The Journal of Organic Chemistry, Vol. 68, Issue 1, p. 174-176 https://doi.org/10.1021/jo026570u	journal	November 2002
Probing Protein Electrostatics with a Synthetic Fluorescent Amino Acid Cohen, B. E. Science, Vol. 296, Issue 5573 https://doi.org/10.1126/science.1069346	journal	May 2002
Main conformer of gaseous glycine: molecular structure and rotational barrier from electron diffraction data and rotational constants Iijima, Kinya; Tanaka, Kumiko; Onuma, Shigeki Journal of Molecular Structure, Vol. 246, Issue 3-4 https://doi.org/10.1016/0022-2860(91)80132-N	journal	June 1991
Conformers of gaseous glycine Csaszar, Attila G. Journal of the American Chemical Society, Vol. 114, Issue 24 https://doi.org/10.1021/ja00050a041	journal	November 1992
Glycine conformational analysis Hu, Ching Han; Shen, Mingzuo; Schaefer, Henry F. Journal of the American Chemical Society, Vol. 115, Issue 7 https://doi.org/10.1021/ja00060a046	journal	April 1993
Shape of Glycine Godfrey, Peter D.; Brown, Ronald D. Journal of the American Chemical Society, Vol. 117, Issue 7 https://doi.org/10.1021/ja00112a015	journal	February 1995
Molecular structures of the two most stable conformers of free glycine: Molecular Structures of the Two Most Stable Conformers of Free Glycine Kasalová, Veronika; Allen, Wesley D.; Schaefer, Henry F. Journal of Computational Chemistry, Vol. 28, Issue 8 https://doi.org/10.1002/jcc.20680	journal	March 2007
Conformational Equilibrium in Glycine: Experimental Jet-Cooled Raman Spectrum Balabin, Roman M. The Journal of Physical Chemistry Letters, Vol. 1, Issue 1 https://doi.org/10.1021/jz900068n	journal	November 2009
Conformational study of sarcosine as probed by matrix-isolation FT-IR spectroscopy and molecular orbital calculations Gómez-Zavaglia, A.; Fausto, R. Vibrational Spectroscopy, Vol. 33, Issue 1-2 https://doi.org/10.1016/S0924-2031(03)00095-X	journal	December 2003
The shape of neutral sarcosine in gas phase Cocinero, Emilio J.; Villanueva, Pablo; Lesarri, Alberto Chemical Physics Letters, Vol. 435, Issue 4-6 https://doi.org/10.1016/j.cplett.2006.12.067	journal	February 2007
Gas-Phase Structure ofN,N-Dimethylglycine Lesarri, Alberto; Cocinero, Emilio J.; López, Juan C. ChemPhysChem, Vol. 6, Issue 8 https://doi.org/10.1002/cphc.200500103	journal	August 2005
A theoretical investigation of the dictating forces in small amino acid conformational preferences: The case of glycine, sarcosine and N,N-dimethylglycine Cormanich, Rodrigo A.; Ducati, Lucas C.; Tormena, Cláudio F. Chemical Physics, Vol. 421 https://doi.org/10.1016/j.chemphys.2013.05.007	journal	June 2013
Spectroscopic Signature of Proton Location in Proton Bound HSO ₄ ^– ·H ⁺ ·X ^– (X = F, Cl, Br, and I) Clusters Hou, Gao-Lei; Wang, Xue-Bin The Journal of Physical Chemistry Letters, Vol. 10, Issue 21 https://doi.org/10.1021/acs.jpclett.9b02663	journal	October 2019
Probing Orientation-Specific Charge–Dipole Interactions between Hexafluoroisopropanol and Halides: A Joint Photoelectron Spectroscopy and Theoretical Study Wang, Lei; Yuan, Qinqin; Cao, Wenjin The Journal of Physical Chemistry A, Vol. 124, Issue 10 https://doi.org/10.1021/acs.jpca.0c00024	journal	February 2020
Cryogenic and temperature-dependent photoelectron spectroscopy of metal complexes Yuan, Qinqin; Cao, Wenjin; Wang, Xue-Bin International Reviews in Physical Chemistry, Vol. 39, Issue 1 https://doi.org/10.1080/0144235X.2020.1719699	journal	January 2020
On the spin-orbit splitting of the rare gas-monohalide molecular ground state Haberland, Hellmut Zeitschrift f�r Physik A Atoms and Nuclei, Vol. 307, Issue 1 https://doi.org/10.1007/BF01416070	journal	March 1982
Study of the I·CO ₂ van der Waals complex by threshold photodetachment spectroscopy of I ^– CO ₂ Zhao, Yuexing; Arnold, Caroline C.; Neumark, Daniel M. J. Chem. Soc., Faraday Trans., Vol. 89, Issue 10 https://doi.org/10.1039/FT9938901449	journal	January 1993
Study of halogen–carbon dioxide clusters and the fluoroformyloxyl radical by photodetachment of X ⁻ (CO ₂ ) (X=I,Cl,Br) and FCO ⁻ ₂ Arnold, Don W.; Bradforth, Stephen E.; Kim, Eun H. The Journal of Chemical Physics, Vol. 102, Issue 9 https://doi.org/10.1063/1.468575	journal	March 1995
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

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