Pharmaceutical salts and cocrystals involving amino acids: A brief structural overview of the state-of-art

European Journal of Medicinal Chemistry

Volumn 74, Issue , 2014, Pages 411-426

  Tilborg, Anaëlle ^a   Norberg, Bernadette ^a   Wouters, Johan ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

Active pharmaceutical ingredient (API); Amino acids; Coformer; Drug substance; Patent rights; Pharmaceutical cocrystal; Therapeutic salt

Indexed keywords

AMINO ACID; AMPHOLYTE; COUNTERION; NEW DRUG; PROLINE; SODIUM CHLORIDE;

ARTICLE; CASE STUDY; CRYSTAL; DRUG FORMULATION; DRUG MARKETING; HUMAN; MEDICAL LITERATURE; MEDICAL RESEARCH; MOLECULE; PHARMACEUTICS;

ACTIVE PHARMACEUTICAL INGREDIENT (API); AMINO ACIDS; COFORMER; DRUG SUBSTANCE; PATENT RIGHTS; PHARMACEUTICAL COCRYSTAL; THERAPEUTIC SALT;

AMINO ACIDS; CRYSTALLIZATION; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS;

EID: 84893283820     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.11.045     Document Type: Short Survey

References (165)

1. P.H. Stahl, and C.G. Wermuth Handbook of Pharmaceutical Salts, Properties, Selection and Use 2008 Wiley-VCH, IUPAC NY, USA
2. A.V. Trask, W.D.S. Motherwell, and W. Jones Physical stability enhancement of theophylline via cocrystallization Int. J. Pharm. 320 2007 114 123
3. Y. Qiu, Y. Chen, G.Z. Zhang, L. Liu, and W. Porter Developing Solid Oral Dosage Forms 2009 Elsevier NY, USA
4. R. Hilfiker Polymorphism in the Pharmaceutical Industry 2006 Wiley-VCH Germany
5. J. Wouters, and L. Quéré Pharmaceuticals Salts and Cocrystals 2012 RSC Publishing Oxford, UK
6. A.L. Weber, and S.L. Miller Reasons for the occurrence of the twenty coded protein amino acids J. Mol. Evol. 17 5 1981 273 284
7. J. Kyte, and R.F. Doolittle A simple method for displaying the hydropathic character of a protein J. Mol. Biol. 157 1982 105 132
8. R.F. Doolittle Redundancies in protein sequence G.D. Fasman, Prediction of Protein Structures and the Principles of Protein Conformation 1989 Plenum Press NY 599 623
9. J.P. Hamend, and H.C. Helgeson Solubilities of the common l-α-amino acids as a function of temperature and solution pH Pure Appl. Chem. 69 1997 935 942
10. D.J. Ager, D.P. Pantaleone, S.A. Henderson, A.R. Katritzky, I. Prakash, and D.E. Walters Commercial, synthetic non-nutritive sweeteners Angew. Chem. Int. Ed. 37 13-24 1998 1802 1817
11. Pallas 3.7.1.2 1994 2006 CompuDrug Chemistry Ltd., Copyright © CompuDrug
12. L. Borgström, B. Kågedal, and O. Paulsen Pharmacokinetics of N-acetylcysteine in man Eur. J. Clin. Pharm. 31 2 1986 217 222
13. F.W. Flitney, R.J. Pritchard, G.D. Kennovin, S.K. Bisland, D.G. Hirst, and S.P. Fricker Antitumor actions of ruthenium(III)-based nitric oxide scavengers and nitric oxide synthase inhibitors Mol. Cancer Ther. 10 9 2011 1571 1580
14. B. Dalhus, and C.H. Görbitz Molecular aggregation in crystalline 1:1 complexes of hydrophobic d- and l-amino acids. I. The l-isoleucine series Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 55 1999 424 431
15. B. Dalhus, and C.H. Görbitz Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic d- and l-amino acids. II. The d-norleucine series Acta Crystallogr. Sect. C Cryst. Struct. Commun. 55 1999 1105 1112
16. B. Dalhus, and C.H. Görbitz 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 Cryst. Struct. Commun. 55 1999 1547 1555
17. C.H. Görbitz, K. Rissanen, A. Valkonen, and A. Husabø 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. 65 2009 o267 o272
18. G. Bastiat, and J.C. Leroux Pharmaceutical organogels prepared from aromatic amino acid derivatives J. Mater. Chem. 19 2009 3867 3877
19. B. Kozier, G. Erb, A.J. Herman, K. Burke, S.R. Bouchal, and S.P. Hirst Fundamentals of Nursing: The Nature of Nursing Practice in Canada Canadian ed. 2004 Prentice Hall Health Toronto, Canada
20. R.E.C. Wildman Handbook of Nutraceuticals and Functional Foods first ed. 2001 CRC Press Series (Modern Nutrition) Boca Raton, Florida, USA
21. F.H. Allen The Cambridge Structural Database: a quarter million structures and rising Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 58 2002 380 388
22. SciFinder CAS (Chemical Abstracts Service) Web-based Interface from American Chemical Society (ACS) 2013 Copyright © American Chemical Society
23. a, CRC Handbook (2010 version) Boca Raton, Florida, USA.
24. D.M. Salunke, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. IX. Crystal structure of l-ornithine l-aspartate hemihydrate Int. J. Pept. Protein Res. 22 1983 154
25. T. Yamada, X. Liu, U. Englert, H. Yamane, and R. Dronskowski Solid-state structure of free base guanidine achieved at last Chem. Eur. J. 15 23 2009 5651 5655
26. 4 Z. Kristallogr. 179 1987 267 280
27. T.H. Jukes Some historical notes on chlortetracycline Rev. Infect. Dis. 7 5 1985 702 707
28. S. Inouye, and Y. Iitaka Crystallographic data on the molecular complexes of tetracycline salts Acta Crystallogr. 17 1964 207 208
29. B. Peng, Q. Peng, W. Zhou, and Z. Zhou Guanidinium l-glutamate Acta Crystallogr. Sect. E Struct. Rep. Online 66 2010 o2679
30. J.W. Steed, and J.L. Atwood Supramolecular Chemistry second ed. 2009 Wiley-VCH Germany
31. A.N. Chekhlov 1,10-Diazonia-18-crown-6 bis(dl-glutamate) Russ. J. Gen. Chem. 71 2001 119
32. A. Albert Heterocyclic Chemistry second ed. 1968 Athlone Press London, UK
33. C.H. Görbitz, and J. Husdal Cocrystallizing agents for amino acids. I. The crystal structure of l-glutamic acid. 2-Methylimidazole Acta Chem. Scand. 50 1996 796 801
34. S. Bhattacharya, A.K. Bera, S. Ghosh, S. Chakraborty, B.P. Mukhopadhyay, A. Pal, and A. Banerjee Regiospecificity of nucleotide-amino acid mating vs. water dynamics: a key to protein-nucleic acid assemblies: structure of unidecahydrated inosine-5′-monophosphate and l-glutamic acid cocrystal at atomic resolution J. Chem. Cryst. 30 2000 655 663
35. W. Haglund Forensic Taphonomy: The Postmortem Fate of Human Remains 1996 CRC Press Series Boca Raton, Florida, USA
36. S. Ramaswamy, M. Nethaji, and M.R.N. Murthy Crystal structure of putrescine-glutamic acid complex Curr. Sci. 58 1989 1160 1162
37. S. Ramaswamy, and M.R.N. Murthy The crystal and molecular structure of putrescine-di-glutamic acid complexes Curr. Sci. 61 1991 410 412
38. C.G. Suresh, J. Ramaswamy, and M. Vijayan 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 Struct. Crystallogr. Cryst. Chem. 42 1986 473 478
39. J. Soman, M. Vijayan, B. Ramakrishnan, and T.N.G. Row 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 29 1990 533 542
40. D.M. Salunke, and M. Vijayan l-Arginine l-aspartate Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 38 1982 1328 1330
41. J. Soman, C.G. Suresh, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides: XV. Crystal structures of l-lysine d-glutamate and l-lysine d-asparate monohydrate and the effect of chirality on molecular aggregation Int. J. Pept. Protein Res. 32 1988 352 360
42. T.N. Bhat, and M. Vijayan X-ray studies of crystalline complexes involving amino acids. II. The crystal structure of l-arginine l-glutamate Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 33 1977 1754 1759
43. J. Soman, and M. Vijayan 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. 14 1989 111 125
44. V. Bertolasi, P. Gilli, V. Ferretti, and G. Gilli Resonance-assisted 0-H 0 hydrogen bonding: its role in the crystalline self-recognition of b-diketone enols and its structural and IR characterization Chem. Eur. J. 2 8 1996 925 934
45. G.R. Desiraju, and T. Steiner The Weak Hydrogen Bond in Structural Chemistry and Biology International Union of Crystallography (IUCr) Monographs on Crystallography vol. 9 1999 Oxford University Press Inc. New York, USA
46. H.R. Snyder, A.L. Brooks, and S.H. Shapiro Pimelic acid from cyclohexanone Org. Synth. Coll. 2 1943 531
47. A. Müller Pimelic acid from salicylic acid Org. Synth. Coll. 11 1931 42
48. D. Voet, J.G. Voet, and C.W. Pratt Fundamentals of Biochemistry: Life at the Molecular Level second ed. 2006 Wiley & Sons Hoboken, New Jersey, USA
49. N.T. Saraswathi, S. Roy, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. XLI. Commonalities in aggregation and conformation revealed by the crystal structures of the pimelic acid complexes of l-arginine and dl-lysine Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 59 2003 641 646
50. D.M. Salunke, and M. Vijayan Crystal structure of the amino acid-vitamin complex lysine pantothenate Biochim. Biophys. Acta - Gen. Subj. 798 1984 175 179
51. G.I. Brown The Big Bang: a History of Explosives 1998 Sutton Publishing Stroud, UK
52. C.D. Gutsche Calixarenes Revisited 1998 RSC Publishing Cambridge, UK
53. F.L. Carson, and C. Hladik Histotechnology: a Self-instructional Text third ed. 2009 American Society for Clinical Pathology Press USA
54. H. Nagata, Y. In, K. Tomoo, M. Doi, T. Ishida, and A. Wakahara Structural feature and molecular interaction of basic amino acid-picric acid complexes by X-ray crystal analyses Chem. Pharm. Bull. 43 1995 1836 1843
55. M. Selkti, A.W. Coleman, I. Nicolis, N. Douteau-Guevel, F. Villain, A. Tomas, and C. de Rango The first example of a substrate spanning the calix[4]arene bilayer: the solid state complex of p-sulfonatocalix[4]arene with l-lysine Chem. Commun. 2000 161 162
56. W.H. Ojala, E.A. Sudbeck, L.K. Lu, T.I. Richardson, R.E. Lovrien, and W.B. Gleason Complexes of lysine, histidine, and arginine with sulfonated azo dyes: model systems for understanding the biomolecular recognition of glycosaminoglycans by proteins J. Am. Chem. Soc. 118 1996 2131 2142
57. Merck Index tenth ed. 1983 0-911910-27-1
58. A. Avdeef, D.A. Barrett, P.N. Shaw, R.D. Knaggs, and S.S. Davis Octanol-, chloroform-, and propylene glycol dipelargonat-water partitioning of morphine-6-glucuronide and other related opiates J. Med. Chem. 39 22 1996 4377 4381
59. J. Sangster Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry 1994 Wiley & Sons New York, USA
60. M.E. Falagas, A.P. Grammatikos, and A. Michalopoulos Potential of old-generation antibiotics to address current need for new antibiotics Expert Rev. Anti-Infect. Ther. 6 5 2008 593 600
61. L. Zhao, and C.H. Ball Determination of Chloramphenicol, Florfenicol, and Thiamphenicol in Honey Using Agilent SampliQ OPT Solid-phase Extraction Cartridges and Liquid Chromatography-tandem Mass Spectrometry, Application Notes in Food Safety 2009 Agilent Technologies
62. Merck Index twelfth ed. 1996 0-911910-12-3
63. L.P. Garrod Relative antibacterial activity of three penicillins Br. Med. J. 1 5172 1960 527 529
64. G. Kortüm, W. Vogel, and K. Andrussar Pure Appl. Chem. 1 1961 187 188
65. P.F. Schellhammer An evaluation of bicalutamide in the treatment of prostate cancer Expert Opin. Pharmacother. 3 9 2002 1313 1328
66. D.C. Hooper Quinolone Antimicrobial Agents third ed. 2003 ASM Press USA
67. W. Sneader The discovery of aspirin: a reappraisal BMJ - Clin. Res. 321 7276 2000 1591 1594
68. J.P. Bounhoure, G. Bottineau, and P. Lechat Value of perindopril in the treatment of chronic congestive heart failure: multicentre double-blind placebo-controlled study Clin. Exp. Hypertens. A11 Suppl. 2 1989 575 586
69. B.K. Skrumsager, K.K. Nielsen, M. Müller, G. Pabst, P.G. Drake, and B. Edsberg Ragaglitazar: the pharmacokinetics, pharmacodynamics, and tolerability of a novel dual PPAR alpha and gamma agonist in healthy subjects and patients with type 2 diabetes J. Clin. Pharmacol. 43 11 2003 1244 1256
70. S. Ebdrup, I. Pettersson, H.B. Rasmussen, H.J. Deussen, A.F. Jensen, S.B. Mortensen, J. Fleckner, L. Pridal, L. Nygaard, and P. Sauerberg Synthesis and biological and structural characterization of the dual-acting peroxisome proliferator-activated receptor α/γ agonist ragaglitazar J. Med. Chem. 46 2003 1306 1317
71. J. Garau Other antimicrobials of interest in the era of extended-spectrum beta-lactamases: fosfomycin, nitrofurantoin and tigecycline Clin. Microbiol. Infect. 14 Suppl. 1 2008 198 202
72. S. Cherukuvada, N.J. Babu, and A. Nangia Nitrofurantoin-p-aminobenzoic acid cocrystal: hydration stability and dissolution rate studies J. Pharm. Sci. 100 2011 3233 3244
73. A. Tilborg, G. Springuel, B. Norberg, J. Wouters, and T. Leyssens Structural study of prolinium/fumaric acid zwitterionic cocrystals: focus on hydrogen-bonding pattern involving zwitterionic (ionic) heterosynthons Cryst. Growth Des. 13 6 2013 2373 2389
74. A. Tilborg, G. Springuel, B. Norberg, J. Wouters, and T. Leyssens On the influence of using a zwitterionic coformer for cocrystallization: structural focus on naproxen-proline cocrystals CrystEngComm 15 17 2013 3341 3350
75. M.N. Johnson, and N. Feeder d-Histidinium (2S,3S)-tartrate Acta Crystallogr. Sect. E Struct. Rep. Online 60 2004 o1374 o1375
76. K. Rajagopal, R.V. Krishnakumar, M.S. Nandhini, and S. Natarajan l-Histidinium hemihydrochloride tartrate tartaric acid dehydrate Acta Crystallogr. Sect. E Struct. Rep. Online 59 2003 o955 o958
77. M.K. Marchewka, S. Debrus, A. Pietraszko, A.J. Barnes, and H. Ratajczak Crystal structure, vibrational spectra and nonlinear optical properties of l-histidinium-l-tartrate hemihydrate J. Mol. Struct. 656 2003 26 273
78. T.N. Bhat, and M. Vijayan X-ray studies of crystalline complexes involving amino acids. III. The structure of the twinned pseudosymmetric crystals of a complex between histidine and aspartic acid Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 34 1978 2556 2565
79. J.V. Pratap, R. Ravishankar, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. XXXV. Invariance and variability in amino acid aggregation in the complexes of maleic acid with l-histidine and l-lysine Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 56 2000 690 696
80. S. Suresh, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. XXX. Structural invariance and optical resolution through interactions with an achiral molecule in the histidine complexes of glycolic acid Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 52 1996 876 881
81. F.H. Herbstein, and M. Kapon The crystal structures of trimesic acid, its hydrates and complexes. V. l-(or dl-)Histidinium trimesate-1/3-acetone Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 35 1979 1614 1619
82. T.N. Bhat, and M. Vijayan X-ray studies on crystalline complexes involving amino acids. I. Crystal structure of l-lysine l-aspartate Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 32 1976 891 895
83. G. Addolorato, C. Ancona, E. Capristo, and G. Gasbarrini Metadoxine in the treatment of acute and chronic alcoholism: a review Int. J. Immunopathol. Pharmacol. 16 3 2003 207 214
84. M.N. Rudra, and L.M. Chowdhury Methionine content of cereals and legumes Nature 166 1950 568
85. Center for Food Safety and Applied Nutrition (CFSAN) Numerical Listing of GRAS Notices December 2007 Food and Drug Administration (FDA)
86. S. Aitipamula, R. Banerjee, A.K. Bansal, K. Biradha, M.L. Cheney, A.R. Choudhury, G.R. Desiraju, A.G. Dikundwar, R. Dubey, N. Duggirala, P.P. Ghogale, S. Ghosh, P.K. Goswami, N.R. Goud, R.R.K.R. Jetti, P. Karpinski, P. Kaushik, D. Kumar, V. Kumar, B. Moulton, A. Mukherjee, G. Mukherjee, A.S. Myerson, V. Puri, A. Ramanan, T. Rajamannar, C.M. Reddy, N. Rodriguez-Hornedo, R.D. Rogers, T.N. Guru Row, P. Sanphui, N. Shan, G. Shete, A. Singh, C.C. Sun, J.A. Swift, R. Thaimattam, T.S. Thakur, R.K. Thaper, S.P. Thomas, S. Tothadi, V.R. Vangala, N. Variankaval, P. Vishweshwar, D.R. Weyna, and M.J. Zaworotko Polymorphs, salts, and cocrystals: what's in a name? Cryst. Growth Des. 12 2012 2147 2152
87. S.L. Childs, G.P. Stahly, and A. Park The salt-cocrystal continuum: the influence of crystal structure on ionization state Mol. Pharmacol. 4 3 2007 323 338
88. J.W. Steed The role of co-crystals in pharmaceutical design Trends Pharm. Sci. 34 2013 185 193
89. D. Braga, F. Grepioni, L. Maini, D. Capucci, S. Nanna, J. Wouters, L. Aerts, and L. Quéré Combining piracetam and lithium salts: ionic co-crystals and co-drugs? Chem. Commun. 48 2012 8219 8221
90. S. Basavoju, D. Boström, and S.P. Velaga Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization Pharm. Res. 25 3 2008 530 541
91. D.P. McNamara, S.L. Childs, J. Giordano, A. Iarricio, J. Cassidy, M.S. Shet, R. Mannion, E. O'Donnell, and A. Park Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API Pharm. Res. 23 2006 1888 1897
92. N. Shan, and M.J. Zaworotko The role of cocrystals in pharmaceutical science Drug. Discov. Today 13 2008 440 446
93. H.G. Brittain Pharmaceutical cocrystals: the coming wave of new drug substances J. Pharm. Sci. 102 2 2013 311 317
94. E.A. Losev, B.A. Zakharov, T.N. Drebushchak, and E.V. Boldyreva Glycinium semi-malonate and a glutaric acid-glycine cocrystal: new structures with short O-HO hydrogen bonds Acta Crystallogr. Sect. C Cryst. Struct. Commun. 67 2011 o297 o300
95. S. Sato d-Glycine nitrate J. Phys. Soc. Jpn. 25 1968 185
96. F.H. Herbstein, M. Kapon, I. Maor, and G.M. Reisner The structure of trimesic acid, its hydrates and complexes. VI. Glycine-trimesic acid monohydrate Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 37 1981 136 140
97. S. Natarajan, A. Kalyanasundar, J. Suresh, S.A.M.B. Dhas, and P.L.N. Lakshman Glycinium hydrogen fumarate glycine solvate monohydrate Acta Crystallogr. Sect. E Struct. Rep. Online 65 2009 o462
98. V.V. Gharzaryan, M. Fleck, and A.M. Petrosya Crystal structures and vibrational spectra of novel compounds with dimeric glycine glycinium cations J. Mol. Struct. 977 2010 117 129
99. M.I. Kay, and R. Kleinberg The crystal structure of triglycine sulfate Ferroelectrics 5 1973 45 52
100. Hao Chen, Lin Xue, Yun-Xia Che, and Ji-Min Zheng Glycine 3,5-dihydroxybenzoic acid monohydrate Chin. J. Struct. Chem. 25 2006 229
101. Y. Takahashi, and I. Fujii (R)-2-(Phenoxy)propionic acid (S)-alanine Anal. Sci. X-ray Struct. Anal. Online 20 2004 x77
102. 2O: a layered inclusion compound J. Struct. Chem. 49 1 2008 188 191
103. H. Nagata, Y. Machida, H. Nishi, M. Kamigauchi, K. Minoura, and T. Ishida (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid d-alanine clathrate Bull. Chem. Soc. Jpn. 82 2009 219
104. Zi-Qiang Hu, Duan-Jun Xu, and Yuan-Zhi Xu (S)-Alanine (S)-mandelic acid Acta Crystallogr. Sect. E Struct. Rep. Online 60 2004 o269
105. M.R. Silva, J.A. Paixao, A.M. Beja, and L.A. da Veiga Strong hydrogen-bonded amino acid dimers in l-alanine alaninium nitrate Acta Crystallogr. Sect. C Cryst. Struct. Commun. 57 2001 838 840
106. Zi-Qiang Hu, Duan-Jun Xu, Yuan-Zhi Xu, Jing-Yun Wu, and M.Y. Chiang (R)-Mandelic acid (S)-alanine hemihydrate Acta Crystallogr. Sect. C Cryst. Struct. Commun. 58 2002 o612 o614
107. Peng Liang Pyridine-2,4-dicarboxylic acid serine Acta Crystallogr. Sect. E Struct. Rep. Online 64 2008 o43
108. Y.I. Smolin, A.E. Lapshin, and G.A. Pankova Bis(l-serine) phosphate monohydrate Russ. Solid State Phys. 45 2003 1803
109. P. Swaminathan, and R. Srinivasan l-Threonine l-allothreonine J. Cryst. Mol. Struct. 5 1975 101
110. I. Fujii, H. Baba, and Y. Takahashi l-(R)-Cysteine l-(S)-mandelic acid Anal. Sci. X-ray Struct. Anal. Online 21 2005 x175
111. M. Alagar, M.S. Nandhini, R.V. Krishnakumar, K. Ravikumar, and S. Natarajan Bis(dl-valine) succinic acid Acta Crystallogr. Sect. E Struct. Rep. Online 60 2004 o1009
112. I. Fujii, T. Watadani, S. Nunomura, and Y. Takahashi (R)-2-Phenoxypropionic acid (S)-valine Anal. Sci. X-ray Struct. Anal. Online 21 2005 x41
113. M. Alagar, R.V. Krishnakumar, M.S. Nandhini, and S. Natarajan Bis(dl-valine) fumaric acid Acta Crystallogr. Sect. E Struct. Rep. Online 59 2003 o857
114. K. Anitha, S. Annavenus, B. Sridhar, and R.K. Rajaram dl-Valine dl-valinium picrate Acta Crystallogr. Sect. E Struct. Rep. Online 60 2004 o1722
115. S. Pandiarajan, B. Sridhar, and R.K. Rajaram l-Valine l-valinium perchlorate monohydrate Acta Crystallogr. Sect. E Struct. Rep. Online 57 2001 o466
116. G.S. Prasad, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. XXI. Structure of a (1:1) complex between l-phenylalanine and d-valine Acta Crystallogr. Sect. C Cryst. Struct. Commun. 47 1991 2603 2606
117. M. Klussmann, T. Izumi, A.J.P. White, A. Armstrong, and D.G. Blackmond Emergence of solution-phase homochirality via crystal engineering of amino acids J. Am. Chem. Soc. 129 2007 7657 7660
118. K. Anitha, S. Athimoolam, and R.K. Rajaram l-Leucine l-leucinium picrate Acta Crystallogr. Sect. E Struct. Rep. Online 61 2005 o1604
119. C.H. Görbitz, B. Dalhus, and G.M. Day l-Allo-Isoleucine d-leucine Phys. Chem. Chem. Phys. (PCCP) 12 2010 8466
120. B. Dalhus, and C.H. Görbitz Structural relationships in crystals accommodating different stereoisomers of 2-amino-3-methylpentanoic acid Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 56 2000 720 727
121. Jian-Rong Su, and Duan-Jun Xu (R)-Methioninium(R)-mandelate (R)-mandelate (R)-mandelic acid Acta Crystallogr. Sect. E Struct. Rep. Online 61 2005 o1933
122. B. Sridhar, N. Srinivasan, B. Dalhus, and R.K. Rajaram l-Methionine l-methioninium perchlorate monohydrate Acta Crystallogr. Sect. E Struct. Rep. Online 58 2002 o779
123. K. Anitha, S. Athimoolam, and R.K. Rajaram dl-Methionine dl-methioninium picrate Acta Crystallogr. Sect. E Struct. Rep. Online 62 2006 o8
124. G.S. Prasad, and M. Vijayan X-ray studies on crystalline complexes involving amino acids and peptides. XXV. Structures of dl-proline hemisuccinic acid and glycyl-l-histidinium semisuccinate monohydrate and a comparative study of amino-acid and peptide complexes of succinic acid Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 49 1993 348 349
125. V.V. Gharzaryan, M. Fleck, and P. Petrosyan l-Prolinium/l-proline tetrafluoroborate Proc. SPIE 7998 2011 79980
126. S. Athimoolam, and S. Natarajan Hydrogen-bonding features in the 1:2 adduct of 4-aminobenzoic acid and l-proline Acta Crystallogr. Sect. C Cryst. Struct. Commun. 63 2007 o283 o286
127. S. Muramulla, H.D. Arman, C.G. Zhao, and E.R.T. Tiekink l-Prolinium methanolate/(S,R,R,R,S,S)-1-[3,5-bis(trifluoromethyl)phenyl]-3-[(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)(6-methoxyquinolin-4-yl)methyl]thiourea Acta Crystallogr. Sect. E Struct. Rep. Online 65 2009 o3070
128. C.R. Ramanathan, and M. Periasamy Resolution of C2-symmetric 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid and 2,3-diphenylsuccinic acid using (S)-proline Tetrahedron: Asymmetry 9 1998 2651 2656
129. S. Pandiarajan, B. Sridhar, and R.K. Rajaram l-prolinium/l-proline perchlorate Acta Crystallogr. Sect. E Struct. Rep. Online 58 2002 o74 o76
130. T.V. Timofeeva, G.H. Kuhn, V.V. Nesterov, V.N. Nesterov, D.O. Frazier, B.G. Penn, and M.Y. Antipin Cocrystal of 1,1-dicyano-2-(4-hydroxyphenyl)-ethene with l-proline and induced conformational polymorphism of 1,1-dicyano-2-(4-hydroxy- 3-methoxyphenyl)-ethene Cryst. Growth Des. 3 2003 383 391
131. P. Rogowska, M.K. Cyranski, A. Sporzynski, and A. Ciesielski Evidence for strong heterodimeric interactions of phenylboronic acids with amino acids Tetrahedron Lett. 47 2006 1389 1393
132. S. Pandiarajan, B. Sridhar, and R.K. Rajaram l-Prolinium l-proline nitrate Acta Crystallogr. Sect. E Struct. Rep. Online 58 2002 o1370 o1371
133. X. Qu, J. Lu, C. Zhao, J.F. Boas, B. Moubaraki, K.S. Murray, A. Siriwardana, A.M. Bond, and L.L. Martin An amino acid derived semiconductor Angew. Chem. Int. Ed. 50 7 2011 1589 1592
134. T.Y. Fu, J.R. Scheffer, and J. Trotter Phenyl[2,4,6-tris(1 methylethyl)phenyl]methanethione and 4-methoxyphenyl[2,4,6-tris(1-methylethyl)phenyl]methanethione Acta Crystallogr. Sect. C Cryst. Struct. Commun. 53 1997 1257 1259
135. G.A. Jeffrey An Introduction to Hydrogen Bonding 1997 Oxford University Press New York, USA
136. C.B. Aakeroy, G.S. Bahra, C.R. Brown, P.B. Hitchcock, Y. Patell, and K.R. Seddon l-Proline 2,5-dihydroxybenzoic acid (1/1): a zwitterion co-crystal Acta Chem. Scand. 49 1995 762 767
137. P.P. Deshpande, J. Singh, A. Pullockaran, T. Kissick, B.A. Ellsworth, J.Z. Gougoutas, J. Dimarco, M. Fakes, M. Reyes, C. Lai, H. Lobinger, T. Denzel, P. Ermann, G. Crispino, M. Randazzo, Z. Gao, R. Randazzo, M. Lindrud, V. Rosso, F. Buono, W.W. Doubleday, S. Leung, P. Richberg, D. Hughes, W.N. Washburn, W. Meng, K.J. Volk, and R.H. Mueller A practical stereoselective synthesis and novel cocrystallizations of an amphiphatic SGLT-2 inhibitor Org. Process Res. Dev. 16 2012 577 585
138. A. Alhalaweh, S. George, S. Basavoju, S.L. Childs, S.A.A. Rizvic, and S.P. Velaga Pharmaceutical cocrystals of nitrofurantoin: screening, characterization and crystal structure analysis CrystEngComm 14 2012 5078 5088
139. 2 Eur. J. Med. Chem. 45 2010 3511 3517
140. K. Lamberts, and U. Englert Structures from MnX2 and proline: isomorphous racemic compounds and a series of chiral non-isomorphous chain polymers Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 68 2012 610 618
141. T.T. Ong, P. Kavuru, T. Nguyen, R. Cantwell, Y. Wojtas, and M.J. Zaworotko 2:1 Cocrystals of homochiral and achiral amino acid zwitterions with Li salts: water-stable zeolitic and diamondoid metal organic materials J. Am. Chem. Soc. 133 2011 9224 9227
142. V.V. Gharzaryan, M. Fleck, and A.M. Petrosyan l-Phenylalaninium l-phenylalanine tetrafluoroborate Proc. SPIE 7998 2011 79980F
143. T. Ishida, M. Doi, and M. Inoue l-Phenylalanine 7-methylguanosine-5′-monophosphate hexahydrate Nucleic Acids Res. 16 1988 6175
144. Zi-Qiang Hu, Duan-Jun Xu, Yuan-Zhi Xu, Jing-Yun Wu, and M.Y. Chiang (R)-Phenylalanine (R)-mandelic acid Chin. J. Struct. Chem. 23 2004 38
145. P.P. Deshpande, L.L. Shen, J.Z. Gougoutas, l-Phenylalanine 2-(4-chloro-3-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol monohydrate, U.S. Patents (2008) USA.
146. Yu-Xi Sun, and Zhong-Lu You 2-Ammonio-3-phenylpropanoic acid 2-ammonio-3-phenylpropanoate sulfate Acta Crystallogr. E60 2004 o1447
147. J. Suresh, R.V. Krishnakumar, and S. Natarajan l-Phenylalanine benzoic acid solvate Acta Crystallogr. Sect. E Struct. Rep. Online 61 2005 o3625
148. C.H. Görbitz, and M.C. Etter Structure of l-phenylalanine l-phenylalaninium formate Acta Crystallogr. Sect. C Cryst. Struct. Commun. 48 1992 1317 1320
149. K. Okamura, K. Aoe, H. Hiramatsu, N. Nishimura, T. Sato, and K. Hashimoto Crystal structures of diastereomeric 1:1 complexes of (R)-and (S)-phenylalanine (S)-mandelic acid Anal. Sci. 13 1997 315 318
150. M. Alagar, R.V. Krishnakumar, K. Rajagopal, M.S. Nandhini, and S. Natarajan l-Phenylalanine fumaric acid Acta Crystallogr. Sect. E Struct. Rep. Online 59 2003 o952
151. M. Alagar, R.V. Krishnakumar, P.P. Devi, and S. Natarajan l-Phenylalanine l-phenylalaninium malonate Acta Crystallogr. Sect. E Struct. Rep. Online 61 2005 o992
152. V.H. Rodrigues, M.M.R.R. Costa, E. de M. Gomes, E. Nogueira, and M. Belslsey l-Phenylalanine-4-nitrophenol (1/1) Acta Crystallogr. Sect. C Cryst. Struct. Commun. 62 2006 o699 o701
153. K. Anitha, and R.K. Rajaram dl-Phenylalanine dl-phenylalaninium picrate Acta Crystallogr. Sect. E Struct. Rep. Online 61 2005 o589
154. M.T. Reetz, J. Huff, J. Rudolph, K. Tollner, A. Deege, and R. Goddard Highly efficient transport of amino acids through liquid membranes via three-component supramolecules J. Am. Chem. Soc. 116 1994 11588 11589
155. M.A. Elbagerma, H.G.M. Edwards, T. Munshi, M.D. Hargreaves, Pavel Matousek, and I.J. Scowen Characterization of new cocrystals by Raman spectroscopy, powder X-ray diffraction, Differential scanning calorimetry and transmission raman spectroscopy Cryst. Growth Des. 10 2010 2360 2371
156. B. Sridhar, N. Srinivasan, and R.K. Rajaram Bis(l-aspartatic acid) nitrate Acta Crystallogr. Sect. E Struct. Rep. Online 58 2002 o1372
157. Z. Taira, and W.H. Watson The structure of a 1:1 mixed crystal of l-glutamic acid and l-pyroglutamic acid and a refinement of the structure of pyroglutamic acid Acta Crystallogr. Sect. B Struct. Crystallogr. Cryst. Chem. 33 1977 3823 3827
158. S. Natarajan, V. Hema, J.K. Sundar, J. Suresh, and P.L.N. Lakshman 4-Amino-2-ammonio-4-oxobutanoate 2,3-dihydroxysuccinate Acta Crystallogr. Sect. E Struct. Rep. Online 66 2010 o2239
159. T. Friščić, and W. Jones Recent advances in understanding the mechanism of cocrystal formation via grinding Cryst. Growth Des. 9 3 2009 1621 1637
160. M.N. Burnett, and C.K. Johnson ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations 1996 Oak Ridge National Laboratory USA Report ORNL-6895
161. C.R. Plata Salaman, N. Tesson, Co-crystals of Celecoxib and l-proline, European Patent EP 2325172, 2011, Barcelona, München, ES, DE.
162. M. Imamura, K. Nakanishi, R. Shiraki, K. Onda, D. Sasuga, M. Yuda, Cocrystal of C-glycoside derivative and l-proline, US 20090143316 A, 2007, Tokyo, Nagano, JP.
163. B.M. Collman, V. Mascitti, Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives, US 8080580 B2, 2009, CT, USA.
164. M.J. Zaworotko, R.D. Shytle, T.T. Ong, P. Kavuru, R.L. Cantwell, T. Nguyen, A.J. Smith, Lithium compositions, US2012030586, 2012, FL, USA.
165. R.D. Shytle, A.J. Smith, P. Kavuru, and M.J. Zaworotko A novel lithium cocrystal with improved oral bioavailability and targeted brain delivery Cell. Transplant. 21 4 2012 792 797