Identification of Lactam-lactim tautomers of aromatic heterocycles in aqueous solution Using 2D IR spectroscopy

Journal of Physical Chemistry Letters

Volumn 3, Issue 22, 2012, Pages 3302-3306

  Peng, Chunte Sam ^a   Tokmakoff, Andrei ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PYRIDONES; BIOLOGICAL FUNCTIONS; CHEMICAL SPECIES; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT CALCULATION; EXPLICIT WATER; FTIR; HETEROCYCLES; HYDRATION EFFECTS; ROOM TEMPERATURE; VIBRATIONAL MODES;

AROMATIC COMPOUNDS; CHEMICAL PROPERTIES; DENSITY FUNCTIONAL THEORY; EQUILIBRIUM CONSTANTS;

FOURIER TRANSFORM INFRARED SPECTROSCOPY;

EID: 84869386984     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz301706a     Document Type: Article

References (32)

1. 15N Nuclear Magnetic Resonance J. Org. Chem. 2000, 65, 2716-2722 (Pubitemid 30249695)
2. Nemeria, N. S.; Chakraborty, S.; Balakrishnan, A.; Jordan, F. Reaction Mechanisms of Thiamin Diphosphate Enzymes: Defining States of Ionization and Tautomerization of the Cofactor at Individual Steps FEBS J. 2009, 276, 2432-3446
3. Thore, S.; Leibundgut, M.; Ban, N. Structure of the Eukaryotic Thiamine Pyrophosphate Riboswitch with Its Regulatory Ligand Science 2006, 312, 1208-1211 (Pubitemid 43801145)
4. Beak, P. Energies and Alkylations of Tautomeric Heterocyclic Compounds: Old Problems-New Answers Acc. Chem. Res. 1977, 10, 186-192
5. Hass, M. A. S.; Hansen, D. F.; Christensen, H. E. M.; Led, J. J.; Kay, L. E. Characterization of Conformational Exchange of a Histidine Side Chain: Protonation, Rotamerization, and Tautomerization of His61 in Plastocyanin from Anabaena variabilis J. Am. Chem. Soc. 2008, 130, 8460-8470 (Pubitemid 351898567)
6. Vila, J. A.; Arnautova, Y. A.; Scheraga, H. A. Assessing the Fractions of Tautomeric Forms of the Imidazole Ring of Histidine in Proteins as a Function of pH Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 5602-5607
7. Wang, W.; Hellinga, H. W.; Beese, L. S. Structural Evidence for the Rare Tautomer Hypothesis of Spontaneous Mutagenesis Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 17644-17648
8. Jang, Y. H.; Goddard, W. A., III; Noyes, K. T.; Sowers, L. C.; Hwang, S.; Chung, D. S. First Principles Calculations of the Tautomers and pKa Values of 8-Oxoguanine: Implications for Mutagenicity and Repair Chem. Res. Toxicol. 2002, 15, 1023-1035 (Pubitemid 34977268)
9. Goodman, M., F. Mutations Caught in the Act Nature 1995, 378, 237-238
10. Fujimoto, A.; Inuzuka, K.; Shiba, R. Electronic Properties and Π-Π* Absorption Spectrum of 2-Pyridone Bull. Chem. Soc. Jpn. 1981, 54, 2802-2806
11. Katritzky, A. R.; Popp, F. D.; Rowe, J. D. Potentially Tautomeric Pyridines. Part VII. Glutaconimide and Its Methyl Derivatives J. Chem. Soc. B 1966, 562-564
12. Hunter, W. N.; Brown, T.; Anand, N. N.; Kennard, O. Structure of an Adenine-Cytosine Base Pair in DNA and Its Implications for Mismatch Repair Nature 1986, 320, 552-555 (Pubitemid 16045124)
13. Thore, S. p.; Frick, C.; Ban, N. Structural Basis of Thiamine Pyrophosphate Analogues Binding to the Eukaryotic Riboswitch J. Am. Chem. Soc. 2008, 130, 8116-8117 (Pubitemid 351898508)
14. Kuhne, R. O.; Schaffhauser, T.; Wokaun, A.; Ernst, R. R. Study of Transient Chemical Reactions by NMR. Fast Stopped-Flow Fourier Transform Experiments J. Magn. Reson. 1979, 35, 39-67
15. Brown, R. D.; Godfrey, P. D.; McNaughton, D.; Pierlot, A. P. Tautomers of Cytosine by Microwave Spectroscopy J. Am. Chem. Soc. 1989, 111, 2308-2310 (Pubitemid 19082003)
16. Colominas, C.; Luque, F. J.; Orozco, M. Tautomerism and Protonation of Guanine and Cytosine. Implications in the Formation of Hydrogen-Bonded Complexes J. Am. Chem. Soc. 1996, 118, 6811-6821 (Pubitemid 26252023)
17. Mata, S.; Cortijo, V.; Caminati, W.; Alonso, J. L.; Sanz, M. E.; López, J. C.; Blanco, S. Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone J. Phys. Chem. A 2010, 114, 11393-11398
18. Moreno, M.; Miller, W. H. On the Tautomerization Reaction 2-Pyridone ⇌ 2-Hydroxypyridine: An Ab Initio Study Chem. Phys. Lett. 1990, 171, 475-479
19. Hamm, P.; Zanni, M. T. Concepts and Methods of 2D Infrared Spectroscopy; Cambridge Press: Cambridge, U.K.; 2011.
20. Peng, C. S.; Jones, K. C.; Tokmakoff, A. Anharmonic Vibrational Modes of Nucleic Acid Bases Revealed by 2D IR Spectroscopy J. Am. Chem. Soc. 2011, 133, 15650-15660
21. Inuzuka, K.; Fujimoto, A. Theoretical Considerations of the Dimer-Formation Energy and Electronic Structures of the Monomer and Dimer of the 2-Pyridone by the Molecular Orbital Method Bull. Chem. Soc. Jpn. 1982, 55, 2537-2540
22. Bensaude, O.; Chevrier, M.; Dubois, J. E. Lactim-Lactam Tautomeric Equilibriums of 2-Hydroxypyridines. 1. Cation Binding, Dimerization, and Interconversion Mechanism in Aprotic Solvents. A Spectroscopic and Temperature-Jump Kinetic Study J. Am. Chem. Soc. 1978, 100, 7055-7060
23. Forlani, L.; Cristoni, G.; Boga, C.; Todesco, P. E.; Vecchio, E. D.; Selva, S.; Monari, M. Reinvestigation of the Tautomerism of Some Substituted 2-Hydroxypyridines ARKIVOC (Gainesville, FL, U. S.) 2002, 198-215 (Pubitemid 38977503)
24. Weisstuch, A.; Neidig, P.; Testa, A. C. A Fluorescence Study of Hydroxypyridines J. Lumin. 1975, 10, 137-144
25. Lee, C.; Cho, M. Vibrational Dynamics of DNA. II. Deuterium Exchange Effects and Simulated IR Absorption Spectra J. Chem. Phys. 2006, 125, 114509/1-114509/12
26. Michelson, A. Z.; Petronico, A.; Lee, J. K. 2-Pyridone and Derivatives: Gas-Phase Acidity, Proton Affinity, Tautomer Preference, and Leaving Group Ability J. Org. Chem. 2012, 77, 1623-1631
27. 2O Complexes J. Chem. Phys. 2003, 118, 3491-3498
28. Smith, A. W.; Lessing, J.; Ganim, Z.; Peng, C. S.; Tokmakoff, A.; Roy, S.; Jansen, T. L. C.; Knoester, J. Melting of a β-Hairpin Peptide Using Isotope-Edited 2D IR Spectroscopy and Simulations J. Phys. Chem. B 2010, 114, 10913-10924
29. Woutersen, S.; Mu, Y.; Stock, G.; Hamm, P. Hydrogen-Bond Lifetime Measured by Time-Resolved 2D-IR Spectroscopy: N-Methylacetamide in Methanol Chem. Phys. 2001, 266, 137-147 (Pubitemid 32416834)
30. Padermshoke, A.; Katsumoto, Y.; Aida, M. Dimerization and Double Proton Transfer-Induced Tautomerism of 4(3 H)-Pyrimidinone in Solution Studied by IR Spectroscopy and Quantum Chemical Calculations J. Phys. Chem. B 2006, 110, 26388-26395 (Pubitemid 46133361)
31. Chung, H. S.; Khalil, M.; Smith, A. W.; Tokmakoff, A. Transient Two-Dimensional IR Spectrometer for Probing Nanosecond Temperature-Jump Kinetics Rev. Sci. Instrum. 2007, 78, 063101/1-063101/10
32. Jones, K. C.; Ganim, Z.; Peng, C. S.; Tokmakoff, A. Transient Two-Dimensional Spectroscopy with Linear Absorption Corrections Applied to Temperature-Jump Two-Dimensional Infrared J. Opt. Soc. Am. B 2012, 29, 118-129