Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions

Zhu, Guo‐Zhu; Qian, Chen‐Hui; Wang, Lai‐Sheng

doi:10.1002/ange.201903444

Title: Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions

Abstract

Abstract Tautomers of the nucleobases play fundamental roles in spontaneous mutations of DNA. Tautomers of neutral cytosine have been studied in the gas phase, but much less is known about charged species. Here, we report the observation and characterization of three tautomers of deprotonated cytosine anions, [ trans ‐keto‐amino‐N3H‐H8b] (tKAN3H8b ⁻ ), [ cis ‐keto‐amino‐N3H‐H8a] (cKAN3H8a ⁻ ) and [keto‐amino‐H] (KAN1 ⁻ ), produced by electrospray ionization. Excited dipole‐bound states (DBSs) are uncovered for the three anions by photodetachment spectroscopy. Excitations to selected DBS vibrational levels of cKAN3H8a ⁻ and tKAN3H8b ⁻ yield tautomer‐specific resonant photoelectron spectra. The current study provides further insight into tautomerism of cytosine and suggests a new method to study the tautomers of nucleobases using electrospray ionization and anion spectroscopy.

Authors:

Zhu, Guo‐Zhu ^[1]; Qian, Chen‐Hui ^[1];

^[1]

Department of Chemistry Brown University Providence RI 02912 USA

Publication Date:: Tue Apr 30 00:00:00 EDT 2019

Sponsoring Org.:: USDOE

OSTI Identifier:: 1510102

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie

Additional Journal Information:: Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 23; Journal ID: ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Zhu, Guo‐Zhu, Qian, Chen‐Hui, and Wang, Lai‐Sheng. Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions.  Germany: N. p., 2019. 
Web.  doi:10.1002/ange.201903444.

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                    Zhu, Guo‐Zhu, Qian, Chen‐Hui, & Wang, Lai‐Sheng. Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions.  Germany.  https://doi.org/10.1002/ange.201903444

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                    Zhu, Guo‐Zhu, Qian, Chen‐Hui, and Wang, Lai‐Sheng. Tue .  
"Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions".  Germany.  https://doi.org/10.1002/ange.201903444.

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@article{osti_1510102,

  title        = {Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions},

  author       = {Zhu, Guo‐Zhu and Qian, Chen‐Hui and Wang, Lai‐Sheng},

  abstractNote = {Abstract Tautomers of the nucleobases play fundamental roles in spontaneous mutations of DNA. Tautomers of neutral cytosine have been studied in the gas phase, but much less is known about charged species. Here, we report the observation and characterization of three tautomers of deprotonated cytosine anions, [ trans ‐keto‐amino‐N3H‐H8b] (tKAN3H8b − ), [ cis ‐keto‐amino‐N3H‐H8a] (cKAN3H8a − ) and [keto‐amino‐H] (KAN1 − ), produced by electrospray ionization. Excited dipole‐bound states (DBSs) are uncovered for the three anions by photodetachment spectroscopy. Excitations to selected DBS vibrational levels of cKAN3H8a − and tKAN3H8b − yield tautomer‐specific resonant photoelectron spectra. The current study provides further insight into tautomerism of cytosine and suggests a new method to study the tautomers of nucleobases using electrospray ionization and anion spectroscopy.},

  doi          = {10.1002/ange.201903444},

  journal      = {Angewandte Chemie},

  number       = 23,

  volume       = 131,

  place        = {Germany},

  year         = {Tue Apr 30 00:00:00 EDT 2019},

  month        = {Tue Apr 30 00:00:00 EDT 2019}

}

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Title: Tautomer‐Specific Resonant Photoelectron Imaging of Deprotonated Cytosine Anions

Abstract

Citation Formats

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Genetical Implications of the Structure of Deoxyribonucleic Acid
journal, May 1953

Vibrational state-selective autodetachment photoelectron spectroscopy from dipole-bound states of cold 2-hydroxyphenoxide: o − HO(C ₆ H ₄ )O ⁻
journal, March 2015

Tautomerism of cytosine probed by gas phase IR spectroscopy
journal, June 2009

Correlated ab initio study of nucleic acid bases and their tautomers in the gas phase, in a microhydrated environment and in aqueous solution : Part 1. Cytosine
journal, January 2002

The Use of Multidimensional Franck−Condon Simulations to Assess Model Chemistries: A Case Study on Phenol
journal, April 2006

Perspective: Electrospray photoelectron spectroscopy: From multiply-charged anions to ultracold anions
journal, July 2015

Propensity rules for vibration-induced electron detachment of anions
journal, July 1981

Tautomers of cytosine and their excited electronic states: a matrix isolation spectroscopic and quantum chemical study
journal, January 2011

Development of a low-temperature photoelectron spectroscopy instrument using an electrospray ion source and a cryogenically controlled ion trap
journal, July 2008

The design and construction of a high-resolution velocity-map imaging apparatus for photoelectron spectroscopy studies of size-selected clusters
journal, August 2014

Observation of Mode-Specific Vibrational Autodetachment from Dipole-Bound States of Cold Anions
journal, July 2013

All Five Forms of Cytosine Revealed in the Gas Phase
journal, January 2013

Ultrafast Excited-State Dynamics of Hydrogen-Bonded Cytosine Microsolvated Clusters with Protic and Aprotic Polar Solvents
journal, November 2018

Identifying Cytosine-Specific Isomers via High-Accuracy Single Photon Ionization
journal, December 2016

Vibrational Spectroscopy of the Dehydrogenated Uracil Radical by Autodetachment of Dipole-Bound Excited States of Cold Anions
journal, January 2014

Anion spectroscopy of uracil, thymine and the amino-oxo and amino-hydroxy tautomers of cytosine and their water clusters
journal, December 1998

Visualizing transient Watson–Crick-like mispairs in DNA and RNA duplexes
journal, March 2015

Electron affinities of the radicals derived from cytosine
journal, January 2005

Anion photoelectron imaging of deprotonated thymine and cytosine
journal, January 2007

Excited State Dynamics of Cold Protonated Cytosine Tautomers: Characterization of Charge Transfer, Intersystem Crossing, and Internal Conversion Processes
journal, August 2017

Resonant Formation of DNA Strand Breaks by Low-Energy (3 to 20 eV) Electrons
journal, March 2000

Tautomerism in cytosine and 3-methylcytosine. A thermodynamic and kinetic study
journal, September 1976

T HEORY OF D IPOLE -B OUND A NIONS
journal, October 2003

The nucleobase cytosine and the cytosine dimer investigated by double resonance laser spectroscopy and ab initio calculations
journal, January 2003

Observation of Dipole-Bound States of Negative Ions
journal, June 1984

Autodetachment spectroscopy and dynamics of vibrationally excited dipole‐bound states of H ₂ CCC ⁻
journal, December 1996

Spectroscopy and dynamics of the dipole‐bound state of acetaldehyde enolate
journal, December 1984

Threshold resonances in the electron photodetachment spectrum of acetaldehyde enolate anion. Evidence for a low‐lying, dipole‐supported state
journal, April 1981

Electron Attachment to the Gas-Phase DNA Bases Cytosine and Thymine
journal, August 2004

Conformation-selective resonant photoelectron imaging from dipole-bound states of cold 3-hydroxyphenoxide
journal, July 2017

All Five Forms of Cytosine Revealed in the Gas Phase
journal, January 2013

Conformation-Selective Resonant Photoelectron Spectroscopy via Dipole-Bound States of Cold Anions
journal, May 2015

Resonant photoelectron imaging of deprotonated uracil anion via vibrational levels of a dipole-bound excited state
journal, January 2017

Ionization of Molecules at Low Energies
journal, August 1966

Excited-State Dynamics of Cytosine Tautomers
journal, November 2009

Spontaneous tunneling and near-infrared-induced interconversion between the amino-hydroxy conformers of cytosine
journal, February 2012

Photoelectron spectroscopy of adiabatically bound valence anions of rare tautomers of the nucleic acid bases
journal, November 2007

Deprotonated guanine·cytosine and 9-methylguanine·cytosine base pairs and their “non-statistical” kinetics: a combined guided-ion beam and computational study
journal, January 2016