The Journal of Physical Chemistry A
Article
(
17) Aliev, A. E.; Courtier-Murias, D. Conformational Analysis of L-
AUTHOR INFORMATION
150.
■
Prolines in Water. J. Phys. Chem. B 2007, 111, 14034−14042.
(
Mechanical and NMR Studies of Ring Puckering and cis/trans-
Rotameric Interconversion in Prolines and Hydroxyprolines. J. Phys.
Chem. A 2009, 113, 10858−10865.
18) Aliev, A. E.; Bhandal, S.; Courtier-Murias, D. Quantum
*
3
Notes
The authors declare no competing financial interest.
(19) Cormanich, R. A.; Ducati, L. C.; Tormena, C. F.; Rittner, R. A
Theoretical Investigation of the Dictating Forces in Small Amino Acid
Conformational Preferences: The Case of Glycine, Sarcosine and N,N-
Dimethylglycine. Chem. Phys. 2013, 421, 32−38.
ACKNOWLEDGMENTS
The authors thank a grant #2012/03933-5 from Sao
Research Foundation (FAPESP) for financial support of this
work and for a scholarship (to C.B.B. #2012/18567-4). Thanks
also go to Conselho Nacional de Pesquisa (CNPQ) for the
fellowships (to R.R. and C.F.T).
■
̃
Paulo
(20) Cormanich, R. A.; Ducati, L. C.; Rittner, R. The Lack of
Intramolecular Hydrogen Bonding and the Side Chain Effect in Alanine
Conformers. J. Mol. Struct. 2012, 1014, 12−16.
(21) Cormanich, R. A.; Ducati, L. C.; Rittner, R. Are Hydrogen Bonds
Responsible for Glycine Conformational Preferences? Chem. Phys.
2
011, 387, 85−91.
REFERENCES
(22) Ananda, K.; Babu, V. V. S. Deprotonation of Hydrochloride Salts
of Amino Acid Esters and Peptide Esters Using Commercial Zinc Dust.
J. Peptide Res. 2001, 57, 223−226.
(23) Uhle, F. C.; Harris, L. S. The Synthesis of α-Methylamino Acids. J.
Am. Chem. Soc. 1956, 78, 381−384.
(24) Yamada, T.; Lukac, P. J.; Yu, T.; Weiss, R. G. Reversible, Room-
Temperature, Chiral Ionic Liquids. Amidinium Carbamates Derived
from Amidines and Amino-Acid Esters with Carbon Dioxide. Chem.
Mater. 2007, 19, 4761−4768.
■
(
1) Gronert, S.; O’Hair, R. A. J. Ab Initio Studies of Amino Acid
Conformations. 1. The Conformers of Alanine, Serine, and Cysteine. J.
Am. Chem. Soc. 1995, 117, 2071−2081.
(
́
2) Lessari, A.; Mata, S.; Cocinero, E. J.; Blanco, S.; Lopez, J. C.;
Alonso, J. L. The Structure of Neutral Proline. Angew. Chem., Int. Ed.
002, 41, 4673−4676.
3) Jaeger, H. M.; Schaefer, H. F., III; Demaison, J.; Csas
2
(
́
zar, A. G.;
Allen, W. D. Lowest-Lying Conformers of Alanine: Pushing Theory to
Ascertain Precise Energetics and Semiexperimental R Structures. J.
(25) GRAMS/AI, version 9.0; ThermoFisher: Wobum, MA, 2009.
(26) Chai, J.-D.; Head-Gordon, M. Long-Range Corrected Hybrid
Density Functionals with Damped Atom−Atom Dispersion Correc-
tions. Phys. Chem. Chem. Phys. 2008, 10, 6615−6620.
e
Chem. Theory Comput. 2010, 6, 3066−3078.
(
́
4) Kapitan, J.; Baumruk, V.; Kopecky, V.; Pohl, R.; Bour, P. Proline
Zwitterion Dynamics in Solution, Glass, and Crystalline State. J. Am.
Chem. Soc. 2006, 128, 13451−13462.
̀
(27) Cances, E.; Mennucci, B.; Tomasi, J. A New Integral Equation
(
5) Schmidt, J.; Kass, S. R. Zwitterion vs Neutral Structures of Amino
Formalism for the Polarizable Continuum Model: Theoretical Back-
ground and Applications to Isotropic and Anisotropic Dielectrics. J.
Chem. Phys. 1997, 107, 3032−3041.
Acids Stabilized by a Negatively Charged Site: Infrared Photo-
dissociation and Computations of Proline−Chloride Anion. J. Phys.
Chem. A 2013, 117, 4863−4869.
6) Lessari, A.; Cocinero, E. J.; Lop
Neutral Valine. Angew. Chem., Int. Ed. 2004, 43, 605−610.
7) Lessari, A.; Sanchez, R.; Cocinero, E. J.; Lopez, J. C.; Alonso, J. L.
Coded Amino Acids in Gas Phase: The Shape of Isoleucine. J. Am. Chem.
Soc. 2005, 127, 12952−12956.
́
8) Alonso, J. L.; Cocinero, E. J.; Lessari, A.; Sanz, M. E.; Lopez, J. C.
(
28) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,
(
́
ez, J. C.; Alonso, J. L. The Shape of
M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.;
Petersson, G. A.; et al. Gaussian 09, revision B.01; Gaussian, Inc.:
Wallingford, CT, 2010.
(
́
́
(
29) NBO, version 5.0, implemented in the Gaussian 09 package of
programs; Gaussian Inc: Wallingford, CT, 2009.
31) Reddy, D. N.; Thirupathi, R.; Tumminakatti, S.; Prabhakaran, E.
(
(
The Glycine−Water Complex. Angew. Chem., Int. Ed. 2006, 45, 3471−
474.
9) Blanco, S.; Sanz, M. E.; Lop
Multiple Structures of Serine. Proc. Natl. Acad. Sci. 2007, 104, 20183−
0188.
10) Cocinero, E. J.; Villanueva, P.; Lessari, A.; Sanz, M. E.; Blanco, S.;
Mata, S.; Lopez, J. C.; Alonso, J. L. The Shape of Neutral Sarcosine in
Gas Phase. Chem. Phys. Lett. 2007, 435, 336−341.
11) Alonso, J. L.; Perez, C.; Sanz, M. E.; Lop
3
(
(
́
ez, J. C.; Alonso, J. L. Revealing the
N. A Method for Stabilizing the cis Prolyl Peptide Bond: Influence of an
Unusual n → π* Interaction in 1,3-Oxazine and 1,3-Thiazine
Containing Peptidomimetics. Tetrahedron Lett. 2012, 53, 4413−4417.
2
(
(
32) Rittner, R.; Ducati, L. C.; Tormena, C. F.; Fiorin, B. C.; Braga, C.
́
B. Conformational Preferences for Some 5-Substituted 2-Acetylth-
iophenes through Infrared Spectroscopy and Theoretical Calculations.
Spectrochim. Acta, Part A 2011, 79, 1071−1076.
(
́
́
ez, J. C. Seven
Conformers of L-Htreonine in the Gas Phase: a LA-MB-FTMW Study.
Phys. Chem. Chem. Phys. 2009, 11, 617−627.
12) Cormanich, R. A.; Ducati, L. C.; Tormena, C. F.; Rittner, R. A
Theoretical and Experimental H NMR Spectroscopy Study of the
Stereoelectronic Interactions That Rule the Conformational Energies of
Alanine and Valine Methyl Ester. J. Phys. Org. Chem. 2013, 26, 849−857.
13) Duarte, C. J.; Cormanich, R. A.; Ducati, L. C.; Rittner, R. H NMR
and Theoretical Studies on the Conformational Equilibrium of
Tryptophan Methyl Ester. J. Mol. Struct. 2013, 1050, 174−179.
14) Deber, C. M.; Brodsky, B.; Rath, A. Proline Residues in Proteins.
In Encyclopedia of Life Sciences; John Wiley & Sons: Chichester, U.K.,
010; pp 1−9.
15) Stepanian, S. G.; Reva, I. D.; Radchenko, E. D.; Adamowicz, L.
(
33) Rittner, R.; Ducati, L. C.; Tormena, C. F.; Fiorin, B. C.; Braga, C.
B.; Abraham, R. J. Studies on the s-cis−trans Isomerism for Some Furan
Derivatives through IR and NMR Spectroscopies and Theoretical
Calculations. Spectrochim. Acta, Part A 2013, 103, 84−89.
(
1
(
34) Ducati, L. C.; Braga, C. B.; Rittner, R.; Tormena, C. F. A Critical
1
Evaluation of the s-cis−trans Isomerism of 2-Acetylpyrrole and Its N-
Methyl Derivative through Infrared and NMR Spectroscopies and
Theoretical Calculations. Spectrochim. Acta, Part A 2013, 116, 196−203.
(
(
35) Rozada, T. C.; Gauze, G. F.; Favaro, D. C.; Rittner, R.; Basso, E. A.
(
Infrared and Theoretical Calculations in 2-Halocycloheptanones
Conformational Analysis. Spectrochim. Acta, Part A 2012, 94, 277−287.
(
2
(
36) Melo, U. Z.; Gauze, G. F.; Bagatin, M. C.; Pontes, R. M.; Basso, E.
Conformers of Nonionized Proline. Matrix-Isolation Infrared and Post-
A. A Theoretical and Experimental Study of the Conformational
Behavior of trans-2-Azidocyclohexanol in Solution. J. Mol. Struct. 2012,
1026, 93−101.
Hartree-Fock ab Initio Study. J. Phys. Chem. A 2001, 105, 10664−10672.
(
16) Haasnoot, C. A. G.; Leeuw, F. A. A. M.; Leeuw, H. P. M.; Altona,
C. Relationship Between Proton−Proton NMR Coupling Constants
and Substituent Electronegativities. III. Conformational Analysis of
Proline Rings in Solution Using a Generalized Karplus Equation.
Biopolymers 1981, 20, 1211−1245.
(37) Karplus, M. Contact Electron-Spin Coupling of Nuclear Magnetic
Moments. J. Chem. Phys. 1959, 30, 11−15.
(38) Hore, P. J. Nuclear Magnetic Resonance; Oxford University Press:
New York, 1995.
1
757
dx.doi.org/10.1021/jp5007632 | J. Phys. Chem. A 2014, 118, 1748−1758