Structural Insights into Bound Water in Crystalline Amino Acids: Experimental and Theoretical 17O NMR

Journal of Physical Chemistry B

Volumn 119, Issue 25, 2015, Pages 8024-8036

  Michaelis, Vladimir K ^a   Keeler, Eric G ^a   Ong, Ta Chung ^a   Craigen, Kimberley N ^b   Penzel, Susanne ^a   Wren, John E C ^b   Kroeker, Scott ^b   Griffin, Robert G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL SHIFT; ELECTRIC FIELDS; MOLECULES; NEUTRON DIFFRACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY;

BIOLOGICAL SOLIDS; BOUND WATER MOLECULES; ELECTRIC FIELD GRADIENTS; MAGNETIC FIELD STRENGTHS; NMR TECHNIQUES; QUANTUM CHEMICAL CALCULATIONS; STRUCTURAL INSIGHTS; X-RAY AND NEUTRON DIFFRACTION;

MAGIC ANGLE SPINNING;

AMINO ACID; OXYGEN; WATER;

CHEMICAL MODEL; CHEMISTRY; COMPARATIVE STUDY; COMPUTER SIMULATION; NEUTRON DIFFRACTION; NUCLEAR MAGNETIC RESONANCE; PROCEDURES; X RAY DIFFRACTION;

AMINO ACIDS; COMPUTER SIMULATION; MODELS, CHEMICAL; NEUTRON DIFFRACTION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXYGEN ISOTOPES; WATER; X-RAY DIFFRACTION;

EID: 84933056271     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b04647     Document Type: Article

References (115)

1. Levy, Y.; Onuchic, J. N. Water and Proteins: A Love-Hate Relationship Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 3325-3326
2. Bondar, A.-N.; Fischer, S.; Smith, J. C. Water Pathways in the Bacteriorhodopsin Proton Pump J. Membr. Biol. 2011, 239, 73-84
3. Luecke, H.; Schobert, B.; Richter, H. T.; Cartailler, J. P.; Lanyi, J. K. Structure of Bacteriorhodopsin at 1.55 Å Resolution J. Mol. Biol. 1999, 291, 899-911
4. Debelouchina, G. T.; Bayro, M. J.; van der Wel, P. C. A.; Caporini, M. A.; Barnes, A. B.; Rosay, M.; Maas, W. E.; Griffin, R. G. Dynamic Nuclear Polarization-Enhanced Solid-State NMR Spectroscopy of GNNQQNY Nanocrystals and Amyloid Fibrils Phys. Chem. Chem. Phys. 2010, 12, 5911-5919
5. van der Wel, P. C. A.; Hu, K. N.; Lewandowski, J.; Griffin, R. G. Dynamic Nuclear Polarization of Amyloidogenic Peptide Nanocrystals: GNNQQNY, a Core Segment of the Yeast Prion Protein Sup35p J. Am. Chem. Soc. 2006, 128, 10840-10846
6. Caporini, M. A.; Bajaj, V. S.; Veshtort, M.; Fitzpatrick, A.; MacPhee, C. E.; Vendruscolo, M.; Dobson, C. M.; Griffin, R. G. Accurate Determination of Interstrand Distances and Alignment in Amyloid Fibrils by Magic Angle Spinning NMR J. Phys. Chem. B 2010, 114, 13555-13561
7. Debelouchina, G. T.; Bayro, M. J.; Fitzpatrick, A. W.; Ladizhansky, V.; Colvin, M. T.; Caporini, M. A.; Jaroniec, C. P.; Bajaj, V. S.; Rosay, M.; MacPhee, C. E. Higher Order Amyloid Fibril Structure by MAS NMR and DNP Spectroscopy J. Am. Chem. Soc. 2013, 135, 19237-19247
8. Fitzpatrick, A. W. P.; Debelouchina, G. T.; Bayro, M. J.; Clare, D. K.; Caporini, M. A.; Bajaj, V. S.; Jaroniec, C. P.; Wang, L.; Ladizhansky, V.; Müller, S. A. Atomic Structure and Hierarchical Assembly of a Cross-β Amyloid Fibril Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 5468-5473
9. Harris, R. K.; Becker, E. D. NMR Nomenclature: Nuclear Spin Properties and Conventions for Chemical Shifts-IUPAC Recommendations J. Magn. Reson. 2002, 156, 323-326
10. Grandinetti, P. J.; Trease, N. M.; Ash, J. T. Symmetry Pathways in Solid State NMR Prog. NMR Spectrosc. 2011, 59, 121-196
11. 17O NMR Studies of Biomolecules Annu. Rep. NMR Spectrosc. 2014, 83, 145-220
12. 17O NMR Studies of Organic and Biological Molecules Prog. Nucl. Magn. Reson. Spectrosc. 2008, 52, 118-169
13. Wu, G. Oxygen 17 NMR Studies of Organic and Biological Molecules. In Encyclopedia of Magnetic Resonance; Wiley: New York, 2011; pp 1-13.
14. 17O NMR: An Introduction to the Background Principles and Applications to Inorganic Materials Chem. Soc. Rev. 2006, 35, 718-735
15. 17O NMR Spectroscopy of Large Protein-Ligand Complexes Angew. Chim. 2010, 49, 8399-8402
16. 17O Multiple-Quantum MAS and Double-Resonance NMR J. Non-Cryst. Solids 2013, 363, 50-56
17. 17O NMR of Pharmaceutical Compounds: Salicyclic Acid and Aspirin J. Phys. Chem. B 2013, 117, 9643-9654
18. 17O NMR Spectroscopy: G-Ribbon and G-Quartet J. Am. Chem. Soc. 2007, 129, 2398-2407
19. 17O} REAPDOR Solid-State NMR Spectroscopy Angew. Chem., Int. Ed. 2012, 51, 10289-10292
20. Prasad, S.; Clark, T. M.; Sharma, R.; Kwak, H. T.; Grandinetti, P. J.; Zimmermann, H. A Combined O-17 RAPT and MQ-MAS NMR Study of L-Leucine Solid State Nucl. Magn. Reson. 2006, 29, 119-124
21. 1H Distance Measurements in Fast Magic-Angle-Spinning Solid-State NMR Spectroscopy for the Determination of Hydrogen Bond Lengths J. Am. Chem. Soc. 2006, 128, 14758-14759
22. Michaelis, V. K.; Markhasin, E.; Daviso, E.; Herzfeld, J.; Griffin, R. G. Dynamic Nuclear Polarization of Oxygen-17 J. Phys. Chem. Lett. 2012, 3, 2030-2034
23. 17O: Direct Polarization J. Phys. Chem. B 2013, 117, 14894-14906
24. Michaelis, V. K.; Ong, T.-C.; Kiesewetter, M. K.; Frantz, D. K.; Walish, J. J.; Ravera, E.; Luchinat, C.; Swager, T. M.; Griffin, R. G. Topical Developments in High Field Dynamic Nuclear Polarization Isr. J. Chem. 2014, 54, 207-221
25. 17O Spectroscopy J. Am. Chem. Soc. 2013, 135, 2975-2978
26. Chmelka, B.; Mueller, K.; Pines, A.; Stebbins, J.; Wu, Y.; Zwanziger, J. O-17 NMR in Solids by Dynamic-Angle Spinning and Double Rotation Nature 1989, 339, 42-43
27. Baltisberger, J. H.; Gann, S. L.; Grandinetti, P. J.; Pines, A. Cross-Polarization Dynamic-Angle Spinning Nuclear-Magnetic-Resonance of Quadrupolar Nuclei Mol. Phys. 1994, 81, 1109-1124
28. Frydman, L.; Harwood, J. S. Isotropic Spectra of Half-Integer Quadrupolar Spins from Bidimensional Magic-Angle-Spinning NMR J. Am. Chem. Soc. 1995, 117, 5367-5368
29. Gan, Z. H. Isotropic NMR Spectra of Half-Integer Quadrupolar Nuclei Using Satellite Transitions and Magic-Angle Spinning J. Am. Chem. Soc. 2000, 122, 3242-3243
30. Wu, G.; Rovnyak, D.; Griffin, R. G. Quantitative Multiple-Quantum Magic-Angle-Spinning NMR Spectroscopy of Quadrupolar Nuclei in Solids J. Am. Chem. Soc. 1996, 118, 9326-9332
31. Wu, G.; Rovnyak, D.; Huang, P. C.; Griffin, R. G. High-Resolution Oxygen-17 NMR Spectroscopy of Solids by Multiple-Quantum Magic-Angle-Spinning Chem. Phys. Lett. 1997, 277, 79-83
32. 17O Solid-State NMR J. Phys. Chem. B 2006, 110, 16089-16101
33. Gullion, T.; Yamauchi, K.; Okonogi, M.; Asakura, T. C-13-O-17 REAPDOR NMR as a Tool for Determining Secondary Structure in Polyamides Macromolecules 2007, 40, 1363-1365
34. 17O Connectivities and Proximities by Solid-State NMR Spectroscopy J. Am. Chem. Soc. 2009, 131, 1820-1834
35. Sefzik, T. H.; Houseknecht, J. B.; Clark, T. M.; Prasad, S.; Lowary, T. L.; Gan, Z.; Grandinetti, P. J. Solid-State O-17 NMR in Carbohydrates Chem. Phys. Lett. 2007, 434, 312-315
36. 17O Sites in Biomaterials Solid State Nucl. Magn. Reson. 2008, 33, 72-75
37. Wu, G.; Dong, S.; Ida, R.; Reen, N. A Solid-State O-17 Nuclear Magnetic Resonance Study of Nucleic Acid Bases J. Am. Chem. Soc. 2002, 124, 1768-1777
38. Yamauchi, K.; Okonogi, M.; Kurosu, H.; Tansho, M.; Shimizu, T.; Gullion, T.; Asakura, T. High Field O-17 Solid-State NMR Study of Alanine Tripeptides J. Magn. Reson. 2008, 190, 327-332
39. 17O NMR Study of L-Tyrosine in Different Ionization States: Implications for Probing Tyrosine Side Chains in Proteins J. Phys. Chem. B 2010, 114, 11681-11688
40. ODell, L. A.; Ratcliffe, C. I.; Kong, X.; Wu, G. Multinuclear Solid-State Nuclear Magnetic Resonance and Density Functional Theory Characterization of Interaction Tensors in Taurine J. Phys. Chem. A 2012, 116, 1008-1014
41. 17O Solid-State NMR Spectroscopy of Biomolecules: A Comprehensive Spectral Analysis of Monosodium L-Glutamate Monohydrate Phys. Chem. Chem. Phys. 2011, 13, 12213-12224
42. Degroot, H. J. M.; Harbison, G. S.; Herzfeld, J.; Griffin, R. G. Nuclear Magnetic Resonance Study of the Schiff-Base in Bacteriorhodopsin-Counterion Effects on the N-15 Shift Anisotropy Biochemistry 1989, 28, 3346-3353
43. Harbison, G.; Herzfeld, J.; Griffin, R. G. N-15 Chemical-Shift Tensors in L-Histidine Hydrochloride Monohydrate J. Am. Chem. Soc. 1981, 103, 4752-4754
44. Munowitz, M.; Bachovchin, W. W.; Herzfeld, J.; Dobson, C. M.; Griffin, R. G. Acid-Base and Tautomeric Equilibria in the Solid-State-N-15 NMR-Spectroscopy of Histidine and Imidazole J. Am. Chem. Soc. 1982, 104, 1192-1196
45. Mackenzie, K. J. D.; Smith, M. E. Multinuclear Solid-State NMR of Inorganic Materials. Pergamon: London, 2002; Vol. 6, p 727.
46. Sternberg, U. The Bond Angle Dependence of the Asymmetry Parameter of the Oxygen-17 Electric Field Gradient Tensor Solid State Nucl. Magn. Reson. 1993, 2, 181-190
47. Slichter, C. P. Principles of Magnetic Resonance. Springer-Verlag: Berlin, Heidelberg, Germany, and New York, 1963; Vol. 1, p 658.
48. Taulelle, F. NMR of Quadrupolar Nuclei in the Solid State. Kluwer Academic Publishers: London, 1988; Vol. 322, p 476.
49. Man, P. P. Encyclopedia of Analytical Chemistry. John Wiley and Sons: Chichester, U.K., 2000; p 12224-12265.
50. Ashbrook, S. E.; Wimperis, S. Quadrupolar Coupling: An Introduction and Crystallographic Aspects. Encyclopedia of Magnetic Resonance; John Wiley & Sons, Ltd.: Chichester, U.K., 2009; pp 1-15.
51. 17O Electric Field Gradient and Chemical Shielding Tensors of the Oxonium Ion in P-Toluenesulfonic Acid Monohydrate J. Phys. Chem. A 2000, 104, 4102-4107
52. 17O NMR Tensors in Potassium Hydrogen Dibenzoate: A Salt Containing a Short OHO Hydrogen Bond Solid State Nucl. Magn. Reson. 2003, 24, 196-208
53. Herzfeld, J.; Berger, A. E. Sideband Intensitites in NMR-Spectra of Samples Spinning at the Magic Angle J. Chem. Phys. 1980, 73, 6021-6030
54. Perdew, J. P.; Burke, K.; Ernzerhof, M. General Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
55. Perdew, J. P.; Burke, K.; Ernzerhof, M. Perdew, Burke, and Ernzerhof Reply Phys. Rev. Lett. 1998, 80, 891-891
56. Vanderbilt, D. Soft Self-Consistent Pseudopotentials in a Generalized Eigenvalue Formalism Phys. Rev. B 1990, 41, 7892-7895
57. Fuess, H.; Hohlwein, D.; Mason, S. A. Neutron Diffraction Study of L-Histidine Hydrochloride Monohydrate Acta Crystallogr. 1977, B33, 654-659
58. Madhaven, J.; Aruna, S.; Thomas, P. C.; Vimalan, M.; Rajasekar, S. A.; Sagayaraj, P. Growth and Characterization of L-Histidine Hydrochloride Monohydrate Single Crystals Cryst. Res. Technol. 2007, 42, 59-64
59. Parthasarathy, R. Crystal Structure of Glycylglycine Hydrochloride Acta Crystallogr. 1969, B25, 509-518
60. Koetzle, T. F.; Hamilton, W. C.; Parthasarathy, R. Precision Neutron Diffraction Structure Determination of Protein and Nucleic Acid Components. II. The Crystal and Molecular Structure of the Dipeptide Glycylglycine Monohydrochloride Monohydrate Acta Crystallogr. 1972, B28, 2083-2090
61. Xian, L.; Lu, G.-X. L-Arginine Hydrochloride Monohydrate Chem. Res. Appl. 2007, 19, 474
62. Flaig, R.; Koritsanszky, T.; Dittrich, B.; Wagner, A.; Luger, P. Intra- and Intermolecular Topological Properties of Amino Acids: A Comparative Study of Experimental and Theoretical Results J. Am. Chem. Soc. 2002, 124, 3407-3417
63. Ramanadham, M.; Sikka, S. K.; Chidambaram, R. Structure of L-Asparagine Monohydrate by Neutron Diffraction Acta Crystallogr. 1972, B28, 3000-3005
64. Ayyar, R. R.; Srinivasan, R. Crystal Structure of L-Cysteine Hydrochloride Monohydrate Curr. Sci. 1965, 34, 449-451
65. Chapman, R. P.; Bryce, D. L. A High-Field Solid-State Cl-35/37 NMR and Quantum Chemical Investigation of the Chlorine Quadrupolar and Chemical Shift Tensors in Amino Acid Hydrochlorides Phys. Chem. Chem. Phys. 2007, 9, 6219-6230
66. Panneerselvam, K.; Soriano-Garcia, M. L-Glycyl-L-Glutamine Monohydrate Acta Crystallogr. 1995, C51, 2718-2720
67. Umadevi, K.; Anitha, K.; Sridhar, B.; Srinivasan, N.; R.K, R. L-Aspartic Acid Monohydrate Acta Crystallogr. 2003, E59, 01073-01075
68. Yates, J. R.; Pickard, C. J.; Payne, M. C.; Mauri, F. Relativisitic Effects Were Included in Castep Calculations at the Level of the Scaler-Relativistic Zeroth-Order Regular Approximation (ZORA) J. Chem. Phys. 2003, 118, 5746
69. Gervais, C.; Dupree, R.; Pike, K. J.; Bonhomme, C.; Profeta, M.; Pickard, C. J.; Mauri, F. Combined First-Principles Computational and Experimental Multinuclear Solid-State NMR Investigation of Amino Acids J. Phys. Chem. A 2005, 109, 6960-6969
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C., Gaussian 03, G03; Gaussian: Pittsburgh, PA, 2003.
71. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B: Condens. Matter 1988, 37, 785-789
72. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
73. Becke, A. D. Density-Functional Thermochemistry. V. Systematic Optimization of Exchange-Correlation Functionals J. Chem. Phys. 1996, 107, 8554-8560
74. Eichele, K. Wsolids NMR Simulation Package, 1.20.21; 2013.
75. Massiot, D.; Fayon, F.; Capron, M.; King, I.; Le Calve, S.; Alonso, B.; Durand, J. O.; Bujoli, B.; Gan, Z.; Hoatson, G. Modelling One and Two-Dimensional Solid-Sate NMR Spectra Magn. Reson. Chem. 2002, 40, 70-76
76. Veshtort, M.; Griffin, R. G. Spinevolution: A Powerful Tool for the Simulation of the Solid and Liquid State NMR Experiments J. Magn. Reson. 2006, 178, 248-282
77. Adiga, S.; Aebi, D.; Bryce, D. L. Efgshield: A Program for Parsing and Summarizing the Results of Electric Field Gradient and Nuclear Magnetic Shielding Tensor Calculations Can. J. Chem. 2007, 85, 496-505
78. Spiess, H. W.; Garrett, B. B.; Sheline, R. K. Oxygen-17 Quarupole Coupling Parameters for Water in Its Various Phases J. Chem. Phys. 1969, 51, 1201
79. 17O NMR and Crystalline Hydrates Solid State Nucl. Magn. Reson. 1996, 7, 147-154
80. Lemaitre, V.; Smith, M. E.; Watts, A. A Review of Oxygen-17 Solid-State NMR of Organic Materials-Towards Biological Applications Solid State Nucl. Magn. Reson. 2004, 26, 215-235
81. 17O NMR of Amino Acids J. Phys. Chem. B 2004, 108, 9256-9263
82. 17O NMR Studies of Amino Acids in the Solid State, in Single and Polycrystalline Forms Int. J. Peptide Protein Res. 1988, 31, 130-136
83. 17O CP MAS NMR Spectroscopy Chem. Commun. 1992, 5, 433-434
84. 17O Solid-State NMR Spectroscopy of Biomolecules: A Comprehensive Spectral Analysis of Monosodium L-Glutamate-Monohydrate Phys. Chem. Chem. Phys. 2011, 13, 12213
85. Yates, J. R.; Pickard, C. J.; Payne, M. C.; Dupree, R.; Profeta, M.; Mauri, F. Theoretical Investigation of Oxygen-17 NMR Shielding and Electric Field Gradients in Glutamic Acid Polymorphs J. Phys. Chem. A 2004, 108, 6032-6037
86. Profeta, M.; Benoit, M.; Mauri, F.; Pickard, C. J. First-Principles Calculation of the O-17 NMR Parameters in Ca Oxide and Ca Aluminosilicates: The Partially Covalent Nature of the Ca-O Bond, a Challenge for Density Functional Theory J. Am. Chem. Soc. 2004, 126, 12628-12635
87. 2: Assignment of the Zeolite Ferrierite Spectrum J. Am. Chem. Soc. 2003, 125, 541-548
88. 17O NMR Studies Allow Quantitative Evaluation of Molecular Dynamics in Organic Solids J. Am. Chem. Soc. 2012, 134, 14609-14617
89. Bonhomme, C.; Gervais, C.; Babonneau, F.; Coelho, C.; Pourpoint, F.; Azaïs, T.; Ashbrook, S. E.; Griffin, J. M.; Yates, J. R.; Mauri, F. First-Principles Calculation of NMR Parameters Using the Gauge Including Projector Augmented Wave Method: A Chemists Point of View Chem. Rev. 2012, 112, 5733-5779
90. Charpentier, T. The PAW/GIPAW Approach for Computing NMR Parameters: A New Dimension Added to NMR Study of Solids Solid State Nucl. Magn. Reson. 2011, 40, 1-20
91. Rees, G. J.; Day, S. P.; Lari, A.; Howes, A. P.; Iuga, D.; Pitak, M. B.; Coles, S. J.; Threlfall, T. L.; Light, M. E.; Smith, M. E. A Multinuclear Solid State NMR, Density Functional Theory and X-Ray Diffraction Study of Hydrogen Bonding in Group I Hydrogen Dibenzoates CrystEngComm 2013, 15, 8823-8839
92. Chiba, T. Deuteron Magnetic Resonance Study of Barium Chlorate Monohydrate J. Chem. Phys. 1963, 39, 947-953
93. 2O J. Mol. Struct. 1979, 52, 95-105
94. Millar, J. M.; Thayer, A. M.; Zax, D. B.; Pines, A. Zero-Field NMR of Small-Amplitude Motions in a Polycrystalline Solid J. Am. Chem. Soc. 1986, 108, 5113-5116
95. Zhao, X.; Harbison, G. S. Deuterium Quadrupolar Tensors of L-Histidine Hydrochloride Monohydrate-D7 J. Phys. Chem. B 2006, 110, 25059-25065
96. Michal, C. A.; Wehman, J. C.; Jelinski, L. W. Deuterium Quadrupole-Coupling and Chemical-Shielding Tensors in the Model Dipeptide Glycylglycine Monohydrochloride Monohydrate J. Magn. Reson., Ser. B 1996, 111, 31-39
97. 2O J. Phys. Chem. A 1997, 101, 988-994
98. 13C Solid-State NMR Correlation Spectroscopy Phys. Chem. Chem. Phys. 2010, 12, 5872-5878
99. Kristensen, J. H.; Farnan, I. Measurement of Molecular Motion in Solids by Nuclear Magnetic Resonance Spectroscopy of Half-Integer Quadrupolar Nuclei J. Chem. Phys. 2001, 114, 9608-9624
100. De Paepe, G. Dipolar Recoupling in Magic Angle Spinning Solid-State Nuclear Magnetic Resonance Annu. Rev. Phys. Chem. 2012, 63, 661-684
101. Griffin, R. G. Dipolar Recoupling in MAS Spectra of Biological Solids Nat. Struct. Biol. 1998, 5, 508-512
102. Wylie, B. J.; Sperling, L. J.; Nieuwkoop, A. J.; Franks, W. T.; Oldfield, E.; Rienstra, C. M. Ultrahigh Resolution Protein Structures Using NMR Chemical Shift Tensors Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 16974-16979
103. Bascunan, J.; Hahn, S.; Park, D.-K.; Iwasa, Y. A 1.3 GHz LTS/HTS NMR Magnet-A Progress Report IEEE Trans. Appl. Supercond. 2011, 21, 2092-2095
104. Benoit, M.; Profeta, M.; Mauri, F.; Pickard, C. J.; Tuckerman, M. E. First-Principles Calculation of the O-17 NMR Parameters of a Calcium Aluminosilicate Glass J. Phys. Chem. B 2005, 109, 6052-6060
105. Wong, A.; Thurgood, G.; Dupree, R.; Smith, M. E. A First-Principles Computational O-17 NMR Investigation of Metal Ion-Oxygen Interactions in Carboxylate Oxygens of Alkali Oxalates Chem. Phys. 2007, 337, 144-150
106. Harris, R. K.; Hodgkinson, P.; Pickard, C. J.; Yates, J. R.; Zorin, V. Chemical Shift Computations on a Crystallographic Basis: Some Reflections and Comments Magn. Reson. Chem. 2007, 45, S174-S186
107. 15N NMR Chemical Shifts of the Glycine Residue of Oligopeptides in the Solid State as Studied by High-Resolution Solid-State NMR Spectroscopy J. Mol. Struct. 1990, 240, 19-29
108. 15N NMR Chemical Shift of the Glycine Residue of Some Oligopeptides in the Solid State J. Mol. Struct. 1991, 245, 69-80
109. Wong, A.; Pike, K. J.; Jenkins, R.; Clarkson, G. J.; Anupold, T.; Howes, A. P.; Crout, D. H. G.; Samoson, A.; Dupree, R.; Smith, M. E. Experimental and Theoretical O-17 NMR Study of the Influence of Hydrogen-Bonding on C=O and O-H Oxygens in Carboxylic Solids J. Phys. Chem. A 2006, 110, 1824-1835
110. Takahashi, A.; Kuroki, S.; Ando, I.; Ozaki, T.; Shoji, A. Hydrogen-Bonded Structure and NMR Parameters of Oxygen-17 Labeled Poly(L-Alanine)S as Studied by Solid State Oxygen-17 NMR Spectroscopy J. Mol. Struct. 1998, 442, 195-199
111. Kuroki, S.; Yamauchi, K.; Ando, I.; Shoji, A.; Ozaki, T. O-17-Isotope Labeling and Hydrogen-Bonded Structure Investigation in Peptides and Polypeptides by Solid State O-17 NMR Curr. Org. Chem. 2001, 5, 1001-1015
112. Chiari, G.; Ferraris, G. The Water Molecule in Crystalline Hydrates Studied by Neutron Diffraction Acta Crystallogr. 1982, B 38, 2331-2341
113. Ganapathy, S.; Delevoye, L.; Arnoureux, J. P.; Madhu, P. K. Heteronuclear Dipolar Decoupling Effects on Multiple-Quantum and Satellite-Transition Magic-Angle Spinning NMR Spectra Magn. Reson. Chem. 2008, 46, 948-954
114. 17O NMR J. Magn. Reson. 2012, 219, 4-12
115. 17O NMR Study of Crystalline Urea: An Example of Large Hydrogen-Bonding Effects J. Phys. Chem. A 2000, 104, 11194-11202