Crystal structures of amino acids: From bond lengths in glycine to metal complexes and high-pressure polymorphs

Crystallography Reviews

Volumn 21, Issue 3, 2015, Pages 160-212

  Görbitz, Carl Henrik ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

amino acid; crystal structure; database; hydrogen bonding; metal complexes; polymorphism

Indexed keywords

CRYSTAL STRUCTURE; DATABASE SYSTEMS; HYDROGEN BONDS; METAL COMPLEXES; METAL IONS; METALS; POLYMORPHISM;

CAMBRIDGE STRUCTURAL DATABASES; DISCOVERY OF X-RAY DIFFRACTIONS; EXTREME TEMPERATURES; HIGH-PRESSURE POLYMORPH; SOLID-STATE STRUCTURES; STRUCTURAL ELEMENTS; X-RAY STRUCTURE DETERMINATIONS;

AMINO ACIDS;

EID: 84930479056     PISSN: 0889311X     EISSN: 14763508     Source Type: Journal    
DOI: 10.1080/0889311X.2014.964229     Document Type: Review

References (186)

1. Görbitz CH. Hydrogen-bond distances and angles in the structures of amino acids and peptides. Acta Crystallogr Sect B. 1989; 45: 390-395. doi: 10.1107/S0108768189003666
2. Suresh CG, Vijayan M. Occurrence and geometrical features of head-to-tail sequences involving amino acids in crystal structures. Int J Pept Protein Res. 1983; 22: 129-143. doi: 10.1111/j.1399-3011.1983.tb02077.x
3. Vinogradov SN. Hydrogen bonds in crystal structures of amino acids, peptides and related molecules. Int J Pept Protein Res. 1979; 14: 281-289. doi: 10.1111/j.1399-3011.1979.tb01934.x
4. Lemanov VV, Popov SN, Pankova GA. Protein amino acid crystals: structure, symmetry, physical properties. Ferroelectrics. 2003; 285: 207-216. doi: 10.1080/00150190390206040
5. Lemanov VV. Ferroelectric and piezoelectric properties of protein amino acids and their compounds. Phys Solid State. 2012; 54: 1841-1842. doi: 10.1134/S1063783412090168
6. Menezes ASd, Santos AOd, Almeida JMA, Sasaki JM, Cardoso LP. Piezoelectric coefficients of l-histidine hydrochloride monohydrate obtained by synchrotron X-ray Renninger scanning. J Phys: Condens Matter. 2007; 19: 106218-1-9.
7. Heredia A, Meunier V, Bdikin IK, Gracio J, Balke N, Jesse S, Tselev A, Agarwal PK, Sumpter BG, Kalinin SV, Kholkin AL. Nanoscale ferroelectricity in crystalline γ-glycine. Adv Funct Mater. 2012; 22: 2996-3003. doi: 10.1002/adfm.201103011
8. Aravindan A, Srinivasan P, Vijayan N, Gopalakrishnan R, Ramasamy P. A comparative study on the growth and characterization of nonlinear optical amino acid crystals: l-Alanine (LA) and l-alanine alaninium nitrate (LAAN). Spectrochim Acta Part A: Mol Biomol Spectrosc. 2008; 71: 297-304. doi: 10.1016/j.saa.2007.12.023
9. Ramasamy G, Meenakshisundaram S. Studies on amino acid picrates: crystal growth, structure and characterization of a new nonlinear optical material l-isoleucinium picrate. Optik-Int J Light Electron Opt. 2014; 125: 4422-4426. doi: 10.1016/j.ijleo.2014.02.036
10. Subramanian N, Neelamagam Rajan D, Sathiya Dhas Martin Britto D, Shanmuganarayanan A. Crystal growth and structure of l-methionine l-methioninium hydrogen maleate-a new NLO material. Sci Technol Adv Mater. 2008; 9: 025012-1-5.
11. Vijayan N, Rajasekaran S, Bhagavannarayana G, Ramesh Babu R, Gopalakrishnan R, Palanichamy M, Ramasamy P. Growth and characterization of nonlinear optical amino acid single crystal: l-alanine. Cryst Growth Des. 2006; 6: 2441-2445. doi: 10.1021/cg049594y
12. Boldyreva EV. Crystalline amino acids. In: Boeyens JCA, Ogilvie JF., editor. Models, mysteries and magic of molecules. Dordrecht: Springer; 2008. p. 167-192.
13. Schade B, Fuhrhop J-H. Amino acid networks. New J Chem. 1998; 22: 97-104. doi: 10.1039/a708317c
14. Toniolo C, Crisma M, Formaggio F. Understanding -amino acid chemistry from X-ray diffraction structures. Peptide Sci. 1996; 40: 627-651. doi: 10.1002/(SICI)1097-0282(1996)40:6<627:AID-BIP4>3.0.CO;2-Y
15. Fleck M, Petrosyan AM. Salts of amino acids: Crystallization, structure and properties. Springer International Publishing; 2014.
16. Allen FH, Motherwell WDS. Applications of the Cambridge Structural Database in organic chemistry and crystal chemistry. Acta Crystallogr Sect B. 2002; 58: 407-422. doi: 10.1107/S0108768102004895
17. Farkas E, Sovago I. Metal complexes of amino acids and peptides. In: Davies JS, editor. Amino acids, peptides and proteins: volume 29. The Royal Society of Chemistry; 1998. p. 324-386.
18. Bernal JD. The crystal structure of the natural amino acids and related compounds. Zeitschrift für Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie. 1931; 78: 363-369.
19. Albrecht G, Corey RB. The crystal structure of glycine. J Am Chem Soc. 1939; 61: 1087-1103. doi: 10.1021/ja01874a028
20. Marsh R. A refinement of the crystal structure of glycine. Acta Crystallogr. 1958; 11: 654-663. doi: 10.1107/S0365110X58001717
21. Iitaka Y. The crystal structure of β-glycine. Acta Crystallogr. 1960; 13: 35-45. doi: 10.1107/S0365110X60000066
22. Iitaka Y. The crystal structure of γ-glycine. Acta Crystallogr. 1961; 14: 1-10. doi: 10.1107/S0365110X61000012
23. Levy HA, Corey RB. The crystal structure of dl-alanine. J Am Chem Soc. 1941; 63: 2095-2108. doi: 10.1021/ja01853a020
24. Donohue J. The crystal structure of dl-alanine. II. Revision of parameters by three-dimensional Fourier analysis. J Am Chem Soc. 1950; 72: 949-953. doi: 10.1021/ja01158a079
25. Shoemaker DP, Donohue J, Schomaker V, Corey RB. The crystal structure of l-threonine. J Am Chem Soc. 1950; 72: 2328-2349. doi: 10.1021/ja01162a002
26. Kartha G, De Vries A. Structure of asparagine monohydrate. Nature. 1961; 192: 862-863. doi: 10.1038/192862a0
27. Karle IL, Karle J. An application of the symbolic addition method to the structure of l-arginine dihydrate. Acta Crystallogr. 1964; 17: 835-841. doi: 10.1107/S0365110X64002250
28. Harding MM, Howieson RM. l-Leucine. Acta Crystallogr Sect B. 1976; 32: 633-634. doi: 10.1107/S0567740876012405
29. Lehmann MS, Nunes AC. A short hydrogen bond between near identical carboxyl groups in the -modification of l-glutamic acid. Acta Crystallogr Sect B. 1980; 36: 1621-1625. doi: 10.1107/S0567740880006711
30. Weissbuch I, Frolow F, Addadi L, Lahav M, Leiserowitz L. Oriented crystallization as a tool for detecting ordered aggregates of water-soluble hydrophobic -amino acids at the air-solution interface. J Am Chem Soc. 1990; 112: 7718-7724. doi: 10.1021/ja00177a036
31. Yamada K, Hashizume D, Shimizu T, Yokoyama S. l-Asparagine. Acta Crystallogr Sect E. 2007; 63: o3802-o3803. doi: 10.1107/S1600536807039505
32. Courvoisier E, Williams PA, Lim GK, Hughes CE, Harris KDM. The crystal structure of l-arginine. Chem Commun. 2012; 48: 2761-2763. doi: 10.1039/c2cc17203h
33. Görbitz CH, Törnroos KW, Day GM. Single-crystal investigation of l-tryptophan with Z ′=16. Acta Crystallogr Sect B. 2012; 68: 549-557. doi: 10.1107/S0108768112033484
34. Williams PA, Hughes CE, Harris KDM. L-Lysine: exploiting powder X-ray diffraction to complete the set of crystal structures of the 20 directly encoded proteinogenic amino acids. Angew Chem Int Ed 2015; 54: doi: 10.1002/anie.201411520.
35. Görbitz CH, Karen P, Petřček V. Phase transitions for enantiomeric amino acids with linear side chains. 2015. In Preparation.
36. Ihlefeldt FS, Pettersen FB, von Bonin A, Zawadzka M, Görbitz CH. The polymorphs of L-phenylalanine. Angew Chem Int Ed 2014; 53: 13600-13604.
37. Langan P, Mason SA, Myles D, Schoenborn BP. Structural characterization of crystals of -glycine during anomalous electrical behaviour. Acta Crystallogr Sect B. 2002; 58: 728-733. doi: 10.1107/S0108768102004263
38. Wilson CC, Myles D, Ghosh M, Johnson LN, Wang W. Neutron diffraction investigations of l-and d-alanine at different temperatures: the search for structural evidence for parity violation. New J Chem. 2005; 29: 1318-1322. doi: 10.1039/b419295h
39. Chitra R, Choudhury RR. Investigation of hydrogen-bond network in bis(glycinium) oxalate using single-crystal neutron diffraction and spectroscopic studies. Acta Crystallogr Sect B. 2007; 63: 497-504. doi: 10.1107/S0108768107016965
40. Rizzato S, Bergès J, Mason SA, Albinati A, Kozelka J. Dispersion-driven hydrogen bonding: predicted hydrogen bond between water and platinum(II) identified by neutron diffraction. Angew Chem Int Ed. 2010; 49: 7440-7443.
41. Mata I, Espinosa E, Molins E, Veintemillas S, Maniukiewicz W, Lecomte C, Cousson A, Paulus W. Contributions to the application of the transferability principle and the multipolar modeling of H atoms: electron-density study of l-histidinium dihydrogen orthophosphate orthophosphoric acid. I. Acta Crystallogr Sect A. 2006; 62: 365-378. doi: 10.1107/S0108767306025141
42. Wilson CC, Henry PF, Schmidtmann M, Ting VP, Williams E, Weller MT. Neutron powder diffraction-new opportunities in hydrogen location in molecular and materials structure. Crystallogr Rev. 2014; 20: 162-206. doi: 10.1080/0889311X.2014.886202
43. Funnell NP, Marshall WG, Parsons S. Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa. CrystEngComm. 2011; 13: 5841-5848. doi: 10.1039/c1ce05487b
44. Wood PA, Francis D, Marshall WG, Moggach SA, Parsons S, Pidcock E, Rohl AL. A study of the high-pressure polymorphs of l-serine using ab initio structures and PIXEL calculations. CrystEngComm. 2008; 10: 1154-1166. doi: 10.1039/b801571f
45. Harding MM, Kariuki BM, Williams L, Anwar J. dl-Norleucine: redetermination of structure and observations with synchrotron radiation Laue diffraction on heating towards transformation. Acta Crystallogr Sect B. 1995; 51: 1059-1062. doi: 10.1107/S0108768195006331
46. Legros J-P, Kvick A. Deformation electron density of -glycine at 120 K. Acta Crystallogr Sect B. 1980; 36: 3052-3059. doi: 10.1107/S0567740880010783
47. Dittrich B, Hubschle CB, Messerschmidt M, Kalinowski R, Girnt D, Luger P. The invariom model and its application: refinement of d, l-serine at different temperatures and resolution. Acta Crystallogr Sect A. 2005; 61: m314-m316. doi: 10.1107/S0108767305005039
48. Dittrich B, Koritsánszky T, Luger P. A simple approach to nonspherical electron densities by using invarioms. Angew Chem Int Ed. 2004; 43: 2718-2721.
49. Dittrich B, Hubschle CB, Propper K, Dietrich F, Stolper T, Holstein JJ. The generalized invariom database (GID). Acta Crystallogr Sect B. 2013; 69: 91-104. doi: 10.1107/S2052519213002285
50. Dittrich B, Sze E, Holstein JJ, Hubschle CB, Jayatilaka D. Crystal-field effects in l-homoserine: multipoles versus quantum chemistry. Acta Crystallogr Sect A. 2012; 68: 435-442. doi: 10.1107/S0108767312013001
51. Mondal S, Prathapa SJ, van Smaalen S. Experimental dynamic electron densities of multipole models at different temperatures. Acta Crystallogr Sect A. 2012; 68: o568-o569. doi: 10.1107/S0108767312029005
52. Moussa SM, Fenton RR, Kennedy BJ, Piltz RO. Hydrogen bonding in cis-bis(l-alaninato)copper(II): a single crystal neutron diffraction study. Inorg Chim Acta. 1999; 288: 29-34. doi: 10.1016/S0020-1693(99)00009-2
53. 2O: a homochiral 1D helical chain hybrid compound with extended Ni-O-Ni bonding. J Am Chem Soc. 2004; 126: 3044-3045. doi: 10.1021/ja031836f
54. Braga D, Chelazzi L, Ciabatti I, Grepioni F. From 3D channelled frameworks to 2D layered structures in molecular salts of l-serine and dl-serine with oxalic acid. New J Chem. 2013; 37: 97-104. doi: 10.1039/C2NJ40379J
55. Williams PA, Hughes CE, Buanz ABM, Gaisford S, Harris KDM. Expanding the solid-state landscape of l-phenylalanine: discovery of polymorphism and new hydrate phases, with rationalization of hydration/dehydration processes. J Phys Chem C. 2013; 117: 12136-12145. doi: 10.1021/jp401547f
56. Boldyreva EV, Ivashevskaya SN, Sowa H, Ahsbahs H, Weber H-P. Effect of hydrostatic pressure on the γ-polymorph of glycine. A polymorphic transition into a new delta-form. Zeitschrift für Kristallographie. 2005; 220: 50-57.
57. Dawson A, Allan DR, Belmonte SA, Clark SJ, David WIF, McGregor PA, Parsons S, Pulham CR, Sawyer L. Effect of high pressure on the crystal structures of polymorphs of glycine. Cryst Growth Des. 2005; 5: 1415-1427. doi: 10.1021/cg049716m
58. Tumanov NA, Boldyreva EV, Ahsbahs H. Structure solution and refinement from powder or single-crystal diffraction data? Pros and cons: an example of the high-pressure-polymorph of glycine. Powder Diffr. 2008; 23: 307-316. doi: 10.1154/1.2999248
59. Boldyreva E. High-pressure diffraction studies of molecular organic solids. A personal view. Acta Crystallogr Sect A. 2008; 64: 218-231. doi: 10.1107/S0108767307065786
60. Moggach SA, Parsons S, Wood PA. High-pressure polymorphism in amino acids. Crystallogr Rev. 2008; 14: 143-184. doi: 10.1080/08893110802037945
61. Görbitz CH. A redetermination of the crystal and molecular structure of Glutathione (γ-l-Glutamyl-l-cysteinylglycine) at 120 K. Acta Chem Scand B. 1987; 41: 362-366. doi: 10.3891/acta.chem.scand.41b-0362
62. Ohanessian J, Avenel D, Neuman A, Gillier-Pandraud H. Structure crystalline de la 2-acétamido-1-N-(l-aspart-4-oyl)-2-désoxy-β-d-glucopyranosylamine. Carbohydr Res. 1980; 80: 1-13. doi: 10.1016/S0008-6215(00)85309-4
63. Ishida T, Morimoto H, Inoue M, Fujiwara T, Tomita K-i. Three-dimensional X-ray crystal structure of S-adenosyl-l-homocysteine, a potent inhibitor of S-adenosylmethionine-dependent methyltransferases. J Chem Soc, Chem Commun. 1981: 671-673. doi: 10.1039/c39810000671
64. Nagata H, Doi M, Inoue M, Ishida T, Kamigauchi M, Sugiura M, Wakahara A. Conformational analysis of the cyclised pyridoxal Schiff base of l-tryptophan. X-ray crystal structure, nuclear magnetic resonance and molecular orbital studies of 3-carboxy-1-{3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridyl}-1,2,3,4-tetrahydro-β-carboline. J Chem Soc, Perkin Trans 2. 1994: 983-988. doi: 10.1039/p29940000983
65. King MD, Buchanan WD, Korter TM. Investigating the anharmonicity of lattice vibrations in water-containing molecular crystals through the Terahertz spectroscopy of l-serine monohydrate. J Phys Chem A. 2010; 114: 9570-9578. doi: 10.1021/jp105384x
66. Bryndal I, Lis T. The structure of O-phospho-D l-threonine in potassium, sodium and ammonium environments. Zeitschrift für Kristallographie. 2006; 221: 139-149. doi: 10.1524/zkri.2006.221.2.139
67. 7-l-cysteato(2-)]disodium]. Acta Crystallogr Sect E. 2011; 67: m1346-m1347. doi: 10.1107/S1600536811035525
68. Zhang YJ, Shu Z, Xu W, Chen G, Li Z-G. l-Glutamic acid hydrochloride at 153 K. Acta Crystallogr Sect E. 2008; 64: o446. doi: 10.1107/S1600536807068560
69. Lehmann M, Koetzle T, Hamilton W. Precision neutron diffraction structure determination of protein and nucleic acid components. VIII: the crystal and molecular structure of the β-form of the amino acid l-glutamic acid. J Cryst Mol Struct. 1972; 2: 225-233. doi: 10.1007/BF01246639
70. Ramaswamy S, Nethaji M, Murthy MRN. Crystal structure of putrecine-glutamic acid complex. Curr Sci. 1989; 58: 1160-1163.
71. Einspahr H, Bugg CE. Calcium-binding to -amino acids: crystal structure of calcium l-glutamate trihydrate. Acta Crystallogr Sect B. 1974; 30: 1037-1043. doi: 10.1107/S0567740874004225
72. Speakman JC. Acid salts of carboxylic acids, crystals with some "Very short" hydrogen bonds. Struct Bond. 1972; 12: 141-199. doi: 10.1007/BFb0117543
73. International Union of Crystallography. Available from: http://www.iucr.org/resources/cif
74. International Union of Crystallography. Available from: http://checkcif.iucr.org/
75. Verbist JJ, Lehmann MS, Koetzle TF, Hamilton WC. Precision neutron diffraction structure determination of protein and nucleic acid components. VI. The crystal and molecular structure of the amino acid l-asparagine monohydrate. Acta Crystallogr Sect B. 1972; 28: 3006-3013. doi: 10.1107/S0567740872007368
76. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA. Mercury CSD 2.0-new features for the visualization and investigation of crystal structures. J Appl Crystallogr. 2008; 41: 466-470. doi: 10.1107/S0021889807067908
77. van de Streek J. Searching the Cambridge Structural Database for the best representative of each unique polymorph. Acta Crystallogr Sect B. 2006; 62: 567-579. doi: 10.1107/S0108768106019677
78. Vela MA, McLaughlin ML, Fronczek FR. An aminocyclohexanecarboxylic acid. Acta Crystallogr Sect C. 1989; 45: 1091-1093. doi: 10.1107/S0108270189000284
79. Codding PW. Structure-activity studies of β-carbolines. 1. Molecular structure and conformation of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate. Can J Chem. 1983; 61: 529-532. doi: 10.1139/v83-092
80. Gainsford GJ, Jackson WG, Sargeson AM. Synthesis and structure of a chiral sulphinamidocobalt(III) complex derived from (R)-cysteine. J Chem Soc, Chem Commun. 1981: 875-877. doi: 10.1039/c39810000875
81. Fitzgerald A, Jensen LH. The crystal and molecular structure of O-diazoacetyl-l-serine (azaserine) at 21°C and 0°C: model error and deterioration. Acta Crystallogr Sect B. 1978; 34: 828-836. doi: 10.1107/S0567740878004136
82. Voogd J, Hulscher JB. Structure of dl-amino-n-butyric acid (modification B): a reinvestigation. Acta Crystallogr Sect B. 1980; 36: 3178-3179. doi: 10.1107/S0567740880011211
83. 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. doi: 10.1021/ja011492y
84. Görbitz CH, Vestli K, Orlando R. A solution to the observed preference in the crystal structures of hydrophobic amino acids. Acta Crystallogr Sect B, Struct Sci. 2009; 65: 393-400. doi: 10.1107/S0108768109014700
85. In Y, Kishima S, Minoura K, Nose T, Shimohigashi Y, Ishida T. Aggregation feature of fluorine-substituted benzene rings and intermolecular C-H···F interaction: crystal structure analyses of mono-and trifluoro-l-phenylalanines. Chem Pharm Bull. 2003; 51: 1258-1263. doi: 10.1248/cpb.51.1258
86. Hübschle CB, Messerschmidt M, Luger P. Crystal structure of dl-tryptophan at 173 K. Cryst Res Technol. 2004; 39: 274-278. doi: 10.1002/crat.200310182
87. Howard-Lock H, Lyne Lock C, Smalley P. The crystal structure of racemic dl-penicillamine and a spectroscopic study of d-(-)-penicillamine. J Crystallogr Spectrosc Res. 1983; 13: 333-353. doi: 10.1007/BF01161297
88. Lesma G, Landoni N, Pilati T, Sacchetti A, Silvani A. Grignard addition to imines derived from Isatine: a method for the asymmetric synthesis of quaternary 3-aminooxindoles. J Org Chem. 2009; 74: 4537-4541. doi: 10.1021/jo900623c
89. Koetzle TF, Lehmann MS, Hamilton WC. Precision neutron diffraction structure determination of protein and nucleic acid components. IX. The crystal and molecular structure of 4-hydroxy-l-proline. Acta Crystallogr Sect B. 1973; 29: 231-236. doi: 10.1107/S0567740873002256
90. Robbers JE, Otsuka H, Floss HG, Arnold EV, Clardy J. Clavicipitic acid: its structure, biosynthesis, and role in ergot alkaloid formation. J Org Chem. 1980; 45: 1117-1121. doi: 10.1021/jo01294a039
91. Kayushina RL, Vainshtein BK. l-Proline. Kristallograpfiya. 1965; 10: 833-844.
92. Grant N, Ward MF, Jaspars M, Harrison WTA. (R)-1,3-Thiazolidin-3-ium-4-carboxylate. Acta Crystallogr Sect E. 2001; 57: o697-o699. doi: 10.1107/S1600536801010947
93. Lynch DE, McClenaghan I. Redetermination of -ammonio-methylpropionoate. Acta Crystallogr Sect E. 2002; 58: o706-o707. doi: 10.1107/S1600536802009662
94. Bell EA, Qureshi MY, Pryce RJ, Janzen DH, Lemke P, Clardy J. 2,4-Methanoproline (2-carboxy-2,4-methanopyrrolidine) and 2,4-methanoglutamic acid (1-amino-1,3-dicarboxycyclobutane) in seeds of Ateleia herbert smithii Pittier (Leguminosae). J Am Chem Soc. 1980; 102: 1409-1412. doi: 10.1021/ja00524a029
95. Valle G, Crisma M, Toniolo C, Sen N, Sukumar M, Balaram P. Crystallographic characterization of the conformation of the 1-aminocyclohexane-1-carboxylic acid residue in simple derivatives and peptides. J Chem Soc, Perkin Trans 2. 1988: 393-398. doi: 10.1039/p29880000393
96. Bhattacharjee SK, Chacko KK, Zand R. Crystal and molecular structure of 4-amino-4-carboxyl thiapyran. J Cryst Mol Struct. 1975; 5: 403-411. doi: 10.1007/BF01291008
97. Görbitz CH, Rissanen K, Valkonen A, Husabø Å. Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic d-and l-amino acids. IV. The l-phenylalanine series. Acta Crystallogr Sect C, Cryst Struct Commun. 2009; 65: o267-o272. doi: 10.1107/S0108270109014309
98. Dalhus B, Görbitz CH. Molecular aggregation in crystalline 1:1 complexes of hydrophobic d-and l-amino acids. I. The l-isoleucine series. Acta Crystallogr Sect B. 1999; 55: 424-431. doi: 10.1107/S0108768198013494
99. Dalhus B, Görbitz CH. Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic d-and l-amino acids. III. The l-leucine and l-valine series. Acta Crystallogr Sect C. 1999; 55: 1547-1555. doi: 10.1107/S0108270199006162
100. Dalhus B, Görbitz CH. Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic d-and l-amino acids. II. The d-norleucine series. Acta Crystallogr Sect C. 1999; 55: 1105-1112. doi: 10.1107/S0108270199003649
101. Görbitz CH, Dalhus B, Day GM. Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals. Phys Chem Chem Phys. 2010; 12: 8466-8477. doi: 10.1039/c004055j
102. Dalhus B. Crystal structures of hydrophobic amino acid complexes-a multivariate analysis of hydrogen bond geometries. Oslo: University of Oslo; 2000.
103. 2O: a layered inclusion compound. J Struct Chem. 2008; 49: 188-191. doi: 10.1007/s10947-008-0028-1
104. Ishida T, Doi M, Inoue M. A selective recognition mode of a nucleic acid base by an aromatic amino acid: l-phenylalanine-7-methylguanosine 5′-monophosphate stacking interaction. Nucleic Acids Res. 1988; 16: 6175-6190. doi: 10.1093/nar/16.13.6175
105. 2O) at atomic resolution. J Chem Crystallogr. 1995; 25: 477-485. doi: 10.1007/BF01665704
106. Smith G, Baldry KE, Kennard CHL, Byriel KA. The preparation and crystal structure of the 1:1 adduct of glycine with urea. Aust J Chem. 1997; 50: 737-740. doi: 10.1071/C96205
107. 3. Acta Crystallogr Sect B. 1977; 33: 3823-3827. doi: 10.1107/S056774087701214X
108. Einspahr H, Gartland GL, Bugg CE. Calcium binding to -amino acids: the crystal structure of calcium l-glutamate chloride monohydrate. Acta Crystallogr Sect B. 1977; 33: 3385-3390. doi: 10.1107/S0567740877011054
109. Nagata H, Machida Y, Nishi H, Kamigauchi M, Minoura K, Ishida T. Structural requirement for chiral recognition of amino acid by (18-Crown-6)-tetracarboxylic acid: binding analysis in solution and solid states. Bull Chem Soc Jpn. 2009; 82: 219-229. doi: 10.1246/bcsj.82.219
110. Reetz MT, Huff J, Rudolph J, Toellner K, Deege A, Goddard R. Highly efficient transport of amino acids through liquid membranes via three-component supramolecules. J Am Chem Soc. 1994; 116: 11588-11589. doi: 10.1021/ja00104a057
111. Prikhodchenko PV, Medvedev AG, Tripol'skaya TA, Churakov AV, Wolanov Y, Howard JAK, Lev O. Crystal structures of natural amino acid perhydrates. CrystEngComm. 2011; 13: 2399-2407. doi: 10.1039/c0ce00481b
112. Churakov AV, Prikhodchenko PV, Howard JAK, Lev O. Glycine and l-serine crystalline perhydrates. Chem Commun. 2009: 4224-4226. doi: 10.1039/b906801e
113. Johnstone RDL, Francis D, Lennie AR, Marshall WG, Moggach SA, Parsons S, Pidcock E, Warren JE. High-pressure polymorphism in l-serine monohydrate: identification of driving forces in high pressure phase transitions and possible implications for pressure-induced protein denaturation. CrystEngComm. 2008; 10: 1758-1769. doi: 10.1039/b810746g
114. Wu Y-F, Li F-F, Jin L-F. 5-Methyl l-glutamate. Acta Crystallogr Sect E. 2005; 61: o3752-o3753. doi: 10.1107/S1600536805032952
115. Yi J-M, Zhang Y-Q, Cong H, Xue S-F, Tao Z. Crystal structures of four host-guest inclusion complexes of ,delta,-tetramethylcucurbit[6]uril and cucurbit[8]uril with some l-amino acids. J Mol Struct. 2009; 933: 112-117. doi: 10.1016/j.molstruc.2009.06.006
116. Etter MC, MacDonald JC, Bernstein J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr Sect B. 1990; 46: 256-262. doi: 10.1107/S0108768189012929
117. Vayá I, Jiménez MC, Miranda MA. Stereodifferentiation in the fluorescence of naproxen-arginine salts in the solid state. Tetrahedron: Asymmetry. 2005; 16: 2167-2171.
118. Dhanalakshmi B, Ponnusamy S, Muthamizhchelvan C. Growth and characterization of a solution grown, new organic crystal: l-histidine-4-nitrophenolate 4-nitrophenol (LHPP). J Cryst Growth. 2010; 313: 30-36. doi: 10.1016/j.jcrysgro.2010.09.049
119. Suresh CG, Ramaswamy J, Vijayan M. X-ray studies of crystalline complexes involving amino acids and peptides. XIII. Effect of chirality on molecular aggregation: The crystal structures of l-arginine d-aspartate and l-arginine d-glutamate trihydrate. Acta Crystallogr Sect B. 1986; 42: 473-478.
120. Soman J, Vijayan M, Ramakrishnan B, Row TNG. X-ray studies on crystalline complexes involving amino acids and peptides. XVII. Chirality and molecular aggregation: the crystal structures of dl-arginine dl-glutamate monohydrate and dl-arginine dl-aspartate. Biopolymers. 1990; 29: 533-542. doi: 10.1002/bip.360290308
121. Soman J, Vijayan M. X-ray studies on crystalline complexes involving amino acids and peptides: Part XVIII. Crystal structure of a new form of l-arginine d-glutamate and a comparative study of amino acid crystal structures containing molecules of the same and mixed chirality. J Biosci. 1989; 14: 111-125. doi: 10.1007/BF02703163
122. Soman J, Suresh CG, Vijayan M. X-ray studies on crystalline complexes involving amino acids and peptides. Int J Pept Protein Res. 1988; 32: 352-360. doi: 10.1111/j.1399-3011.1988.tb01270.x
123. Stern AM, Foxman BM, Tashjian AH, Abeles RH. dl-Threo-β-fluoroaspartate and dl-threo-β-fluoroasparagine: selective cytotoxic agents for mammalian cells in culture. J Med Chem. 1982; 25: 544-550. doi: 10.1021/jm00347a013
124. Rudisill DE, Whitten JP. Synthesis of (R)-4-Oxo-5-phosphononorvaline, an N-Methyl-d-aspartic acid receptor selective ß-keto phosphonate. Synthesis. 1994: 851-854. doi: 10.1055/s-1994-25588
125. Lehmann MS, Verbist JJ, Hamilton WC, Koetzle TF. Precision neutron diffraction structure determination of protein and nucleic acid components. Part V. Crystal and molecular structure of the amino-acid l-arginine dihydrate. J Chem Soc, Perkin Trans 2. 1973: 133-137. doi: 10.1039/p29730000133
126. Kingsford-Adaboh R, Grosche M, Dittrich B, Luger P. dl-Arginine monohydrate at 100 K. Acta Crystallogr Sect C. 2000; 56: 1274-1276. doi: 10.1107/S0108270100010325
127. Suresh S, Padmanabhan S, Vijayan M. X-ray studies on crystalline complexes involving amino acids and peptides. XXVII. Effect of chirality, specific interactions and characteristic aggregation patterns in the structures of arginine and its complexes with formic acid. J Biomol Struct Dyn. 1994; 11: 1425-1435. doi: 10.1080/07391102.1994.10508077
128. Terzyan SS, Karapetyan HA, Sukiasyan RB, Petrosyan AM. l-Arginine nitrates. J Mol Struct. 2004; 687: 111-117. doi: 10.1016/j.molstruc.2003.09.015
129. Moitra S, Kumar Seth S, Kar T. Synthesis, crystal structure, characterization and DFT studies of l-valine l-valinium hydrochloride. J Cryst Growth. 2010; 312: 1977-1982. doi: 10.1016/j.jcrysgro.2010.03.016
130. Mebs S, Messerschmidt M, Luger P. Experimental charge density of an l-phenylalanine formic acid complex with a short hydrogen bond determined at 25 K. Zeitschrift für Kristallographie. 2006; 221: 656-664. doi: 10.1524/zkri.2006.221.9.656
131. Alagar M, Krishnakumar RV, Parimala Devi P, Natarajan S. l-Phenylalanine l-phenylalaninium malonate. Acta Crystallogr Sect E. 2005; 61: o992-o994. doi: 10.1107/S1600536805007014
132. Ghazaryan VV, Fleck M, Petrosyan AM. New salts of amino acids with dimeric cations. Proceedings of SPIE, international conference on laser physics 2010,. 7998:79980F; 2011.
133. Srinivasan N, Sridhar B, Rajaram RK. l-Phenylalanine-nitric acid (2/1). Acta Crystallogr Sect E. 2001; 57: o916-o918. doi: 10.1107/S1600536801014350
134. van Zoeren E, Oonk HAJ, Kroon J. X-ray analysis of l-pyroglutamic acid. A marked case of structural pseudosymmetry. Acta Crystallogr Sect B. 1978; 34: 1898-1900. doi: 10.1107/S0567740878006925
135. Bell RA, Britten JF, Howard-Lock HE, Lock CJL, Schmidt M. The interaction of d-penicillamine with aldehydes and ketones: 2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid. Can J Chem. 1994; 72: 1621-1624. doi: 10.1139/v94-203
136. Kanters JA, Kroon J, Beurskens PT, Vliegenthart JA. The crystal and molecular structure of aminomalonic acid. Acta Crystallogr. 1966; 21: 990-995. doi: 10.1107/S0365110X66004304
137. Bendeif E-e, Jelsch C. The experimental library multipolar atom model refinement of l-aspartic acid. Acta Crystallogr Sect C. 2007; 63: o361-o364. doi: 10.1107/S0108270107021671
138. Low JN, Howie RA, Scrimgeour CM, Watt PW. The structure of l-aminoadipic acid. Acta Crystallogr Sect C. 1988; 44: 1762-1764. doi: 10.1107/S0108270188006997
139. Frey MN, Koetzle TF, Lehmann MS, Hamilton WC. Precision neutron diffraction structure determination of protein and nucleic acid components. X. A comparison between the crystal and molecular structures of l-tyrosine and l-tyrosine hydrochloride. J Chem Phys. 1973; 58: 2547-2556. doi: 10.1063/1.1679537
140. Vasdev N, Chirakal R, Chen JJ, Wilson AA, Houle S, Lough AJ. 3-Hydroxyphenylalanine. Private communication to the Cambridge Structural Database; CCDC 678111, 2008.
141. Mostad A, Rømming C, Tressum L. The crystal and molecular structure of (2-hydroxyphenyl)alanine (o-tyrosine). Acta Chem Scand B. 1975; 29: 171-176. doi: 10.3891/acta.chem.scand.29b-0171
142. Srinivasan N, Sridhar B, Rajaram RK. Hydrogen bis[l-lysinium(2+)] dichloride perchlorate. Acta Crystallogr Sect E. 2001; 57: o875-o877. doi: 10.1107/S1600536801013484
143. Ghazaryan VV, Fleck M, Petrosyan AM. Mixed salts of amino acids: on the vibrational spectra of mixed salts containing a l-lysinium(+)··· l-lysinium(2+) dimeric cation. J Mol Struct. 2010; 982: 145-151. doi: 10.1016/j.molstruc.2010.08.020
144. Srinivasan N, Sridhar B, Rajaram RK. l-lysine l-lysinium dichloride nitrate. Acta Crystallogr Sect E. 2001; 57: o888-o890. doi: 10.1107/S1600536801014040
145. Jiang F, Han W, Wu Y-D. Influence of side chain conformations on local conformational features of amino acids and implication for force field development. J Phys Chem B. 2010; 114: 5840-5850. doi: 10.1021/jp909088e
146. Görbitz CH, Dalhus B. Redetermination of l-leucine at 120 K. Acta Crystallogr Sect C. 1996; 52: 1754-1756. doi: 10.1107/S0108270196002296
147. Melián C, Kremer C, Suescun L, Mombrú A, Mariezcurrena R, Kremer E. Re(V) complexes with amino acids based on the 3+2 approach. Inorg Chim Acta. 2000; 306: 70-77. doi: 10.1016/S0020-1693(00)00151-1
148. Görbitz CH, Leirvåg AB, Jacobsen Ø. Hydrogen bond architecture in structures of N-alkylated hydrophobic amino acids; 2014; 16: 9631-9637.
149. Kapustin EA, Minkov VS, Stare J, Boldyreva EV. One hydrogen bond-two ways to build a structure. The role of N-H···O hydrogen bonds in crystal structures of N,N-dimethylglycine. Cryst Growth Des. 2014; 14: 1851-1864. doi: 10.1021/cg5000183
150. Kraehmer V, Rehder D. Modelling the site of bromide binding in vanadate-dependent bromoperoxidases. Dalton Trans. 2012; 41: 5225-5234. doi: 10.1039/c2dt12287a
151. Nastopoulos V, Germain G, Cordopatis P, Voliotis S. Structure of S-benzyl-l-cysteine methyl ester hydrochloride. Acta Crystallogr Sect C. 1987; 43: 375-376. doi: 10.1107/S0108270187095714
152. Benedetti E, Di Blasio B, Pavone V, Pedone C, Toniolo C, Bonora GM. Self-association of N-protected -amino acids. Optically active and racemic N-tert-butyloxycarbonyl-alanine. Biopolymers. 1981; 20: 1635-1649. doi: 10.1002/bip.1981.360200807
153. Saaby S, Bayón P, Aburel PS, Jørgensen KA. Optically active aromatic and heteroaromatic -amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to -Imino esters. J Org Chem. 2002; 67: 4352-4361. doi: 10.1021/jo0256787
154. Moggach SA, Clark SJ, Parsons S. l-Cysteine-I at 30 K. Acta Crystallogr Sect E. 2005; 61: o2739-o2742. doi: 10.1107/S1600536805023688
155. Kolesov BA, Minkov VS, Boldyreva EV, Drebushchak TN. Phase transitions in the crystals of l-and dl-cysteine on cooling: intermolecular hydrogen bonds distortions and the side-chain motions of thiol-groups. 1. l-Cysteine. J Phys Chem B. 2008; 112: 12827-12839. doi: 10.1021/jp804142c
156. Minkov VS, Tumanov NA, Kolesov BA, Boldyreva EV, Bizyaev SN. Phase transitions in the crystals of l-and dl-cysteine on cooling: the role of the hydrogen-bond distortions and the side-chain motions. 2. dl-Cysteine. J Phys Chem B. 2009; 113: 5262-5272. doi: 10.1021/jp810355a
157. Görbitz CH, Qi L, Mai NTK, Kristiansen H. Redetermined crystal structure of -DL-methionine at 340 K. Acta Crystallogr Sect E. 2014; 70: 337-340. doi: 10.1107/S1600536814022211
158. Taniguchi T, Takaki Y, Sakurai K. The crystal structures of the and β forms of dl-methionine. Bull Chem Soc Jpn. 1980; 53: 803-804. doi: 10.1246/bcsj.53.803
159. Görbitz CH, Alebachew F, Petříiček V. Solid-state phase transitions of dl-aminobutyric acid. J Phys Chem B. 2012; 116: 10715-10721. doi: 10.1021/jp305016k
160. Görbitz CH. Solid-state phase transitions in dl-Norvaline studied by single-crystal X-ray diffraction. J Phys Chem B. 2011; 115: 2447-2453.
161. Coles SJ, Gelbrich T, Griesser UJ, Hursthouse MB, Pitak M, Threlfall T. The elusive high temperature solid-state structure of d, l-Norleucine. Cryst Growth Des. 2009; 9: 4610-4612.
162. Görbitz CH, Karen P., Intricate temperature-induced phase transitions for amino acid quasiracemates. 2015. In preparation.
163. Moggach SA, Allan DR, Morrison CA, Parsons S, Sawyer L. Effect of pressure on the crystal structure of L-serine-I and the crystal structure of L-serine-II at 5.4 GPa. Acta Crystallogr Sect B. 2005; 61: 58-68.
164. Drebushchak TN, Sowa H, Seryotkin YV, Boldyreva EV, Ahsbahs H. l-Serine III at 8.0 GPa. Acta Crystallogr Sect E. 2006; 62: o4052-o4054.
165. Moggach SA, Marshall WG, Parsons S. High-pressure neutron diffraction study of l-serine-I and l-serine-II, and the structure of l-serine-III at 8.1 GPa. Acta Crystallogr Sect B. 2006; 62: 815-825.
166. Moggach SA, Allan DR, Clark SJ, Gutmann MJ, Parsons S, Pulham CR, Sawyer L. High-pressure polymorphism in l-cysteine: the crystal structures of l-cysteine-III and l-cysteine-IV. Acta Crystallogr Sect B. 2006; 62: 296-309.
167. Boldyreva EV, Kolesnik EN, Drebushchak TN, Sowa H, Ahsbahs H, Seryotkin YV. A comparative study of the anisotropy of lattice strain induced in the crystals of dl-serine by cooling down to 100 K, or by increasing pressure up to 8.6 GPa. A comparison with l-serine. Zeitschrift für Kristallographie. 2006; 221: 150-161.
168. Minkov VS, Tumanov NA, Cabrera RQ, Boldyreva EV. Low temperature/high pressure polymorphism in dl-cysteine. CrystEngComm. 2010; 12: 2551-2260.
169. Tumanov NA, Boldyreva EV. X-ray diffraction and Raman study of dl-alanine at high pressure: revision of phase transitions. Acta Crystallogr Sect B. 2012; 68: 412-423.
170. Lozano-Casal P, Allan DR, Parsons S. High-pressure structural study of l-glutamine and the use of Hirshfeld surfaces and graph-set notation to investigate the hydrogen bonding present in the structure up to 4.9 GPa. Acta Crystallogr Sect B. 2008; 64: 466-475.
171. Moggach SA, Allan DR, Parsons S, Sawyer L, Warren JE. The effect of pressure on the crystal structure of hexagonal l-cystine. J Synchrotron Radiat. 2005; 12: 598-607.
172. Johnstone RDL, Lennie AR, Parsons S, Pidcock E, Warren JE. Comparison of the effects of pressure on three layered hydrates: a partially successful attempt to predict a high-pressure phase transition. Acta Crystallogr Sect B. 2009; 65: 731-748.
173. Zakharov BA, Boldyreva EV. A high-pressure single-crystal to single-crystal phase transition in dl-alaninium semi-oxalate monohydrate with switching-over hydrogen bonds. Acta Crystallogr Sect B. 2013; 69: 271-280.
174. Laval G, Clegg W, Crane CG, Hammershoi A, Sargeson AM, Golding BT. Assembly of polyamines via amino acids from three components using cobalt(iii) template methodology. Chem Commun. 2002: 1874-1875.
175. Yamada Y, Inoue M, Miyashita Y, Okamoto K-i, Koikawa M, Tokii T. Effects of counter anions on stereospecific interactions through π-conjugated systems of sulfur-bridged dinuclear cobalt(III)-platinum(II) complexes with optically active penicillaminates: synthetic, structural, and spectroscopic studies. Polyhedron. 2007; 26: 2749-2760.
176. Wang Y-T, Fan H-H, Wang H-Z, Chen X-M. Homochiral helical wavelike (4,4) networks constructed by divalent metal ions and S-carboxymethyl-l-cysteine. J Mol Struct. 2005; 740: 61-67.
177. + core bound to cysteine-derived dipeptides, including Lanthionine. Inorg Chem. 2007; 46: 3385-3394.
178. 2 type ligands. Crystal structure of (+)560CD-((2R,9S)-Diamino-3,3,8,8-tetramethyl-4,7-dithia-1,10-decanedioato)cobalt(III) Ion. Bull Chem Soc Jpn. 1984; 57: 3111-3116.
179. Hirai Y, Nagao Y, Igashira-Kamiyama A, Konno T. Enantioselective/anion-selective incorporation of Tris(ethylenediamine) complexes into 2D coordination spaces between Tripalladium(II) supramolecular layers with d-Penicillaminate. Inorg Chem. 2011; 50: 2040-2042.
180. Glowiak T, Ngoan, DC. Structure of pentaaqua(l-threonine)holmium(III) trichloride. Acta Crystallogr Sect C. 1988; 44: 41-43.
181. Yuan HQ, Igashira-Kamiyama A, Konno T. Aggregation of l-Cysteinato Tricobaltate(III) anions by Lanthanide(III) cations into dimensional structures that are controlled by diastereoisomerism and ionic size. Chem Lett. 2010; 39: 1212-1214.
182. 2 N:O]. Acta Crystallogr Sect E. 2006; 62: m1487-m1488.
183. Corbeil M-C, Beauchamp AL. Conformational changes in serine on methylmercury complexation. Can J Chem. 1988; 66: 1379-1385.
184. Perekalin DS, Karslyan EE, Petrovskii PV, Nelyubina YV, Lyssenko KA, Kononikhin AS, Nikolaev EN, Kudinov AR. Simple synthesis of ruthenium π complexes of aromatic amino acids and small peptides. Chem Eur J. 2010; 16: 8466-8470.
185. 8 O:O ′-bis[tetraaquaterbium(III)] hexaperchlorate. Acta Crystallogr Sect E. 2010; 66: m193-m194.
186. Lamberts K, Möller A, Englert U. Enantiopure and racemic alanine as bridging ligands in Ca and Mn chain polymers. Acta Crystallogr Sect B. 2014; 70: 989-998.