Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

Journal of Chromatography A

Volumn 1269, Issue , 2012, Pages 69-81

  Bertucci, Carlo ^a   Tedesco, Daniele ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Absolute configuration; Anisotropy factor; Drugs; ECD detection system; Enantioselective analysis; Natural products

Indexed keywords

ABSOLUTE CONFIGURATION; ANISOTROPY FACTOR; DETECTION SYSTEM; DRUGS; ENANTIOSELECTIVE ANALYSIS; NATURAL PRODUCTS;

ANISOTROPY; BIOACTIVITY; CHROMATOGRAPHY; DICHROISM; ENANTIOMERS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; STEREOCHEMISTRY; STEREOSELECTIVITY;

FACTOR ANALYSIS;

NATURAL PRODUCT;

ACCURACY; BINDING AFFINITY; BINDING SITE; CHEMICAL BINDING; CHIRALITY; CIRCULAR DICHROISM; CONCENTRATION (PARAMETERS); CONFORMATIONAL TRANSITION; ELECTRONICS; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MATHEMATICAL COMPUTING; OPTICAL ROTATION; PHASE TRANSITION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUALITY CONTROL; QUANTITATIVE ANALYSIS; QUANTUM MECHANICS; RELIABILITY; REVIEW; SENSITIVITY ANALYSIS; STEREOCHEMISTRY;

BIOLOGICAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM;

EID: 84870379843     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2012.09.046     Document Type: Review

References (179)

1. Noyori R. Angew. Chem. Int. Ed. Engl. 2002, 41:2008.
2. Sharpless K.B. Angew. Chem. Int. Ed. Engl. 2002, 41:2024.
3. Berkessel A., Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis 2005, Wiley-VCH, Weinheim.
4. MacMillan D.W.C. Nature 2008, 455:304.
5. Walsh P.J., Kozlowski M.C. Fundamentals of Asymmetric Catalysis 2009, University Science Books, Sausalito.
6. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions 2010, Wiley-VCH, Weinheim. 2nd ed. H.U. Blaser, H.J. Federsel (Eds.).
7. List B. Angew. Chem. Int. Ed. Engl. 2010, 49:1730.
8. Industrial Biotransformations 2006, Wiley-VCH, Weinheim. 2nd ed. A. Liese, K. Seelbach, C. Wandrey (Eds.).
9. Gotor V., Alfonso I., García-Urdiales E. Asymmetric Organic Synthesis with Enzymes 2008, Wiley-VCH, Weinheim.
10. Biocatalysis for the Pharmaceutical Industry: Discovery, Development, and Manufacturing 2009, Wiley & Sons, Singapore. J. Tao, G.Q. Lin, A. Liese (Eds.).
11. Reetz M.T. Angew. Chem. Int. Ed. Engl. 2011, 50:138.
12. Faber K. Biotransformations in Organic Chemistry: A Textbook 2011, Springer, Berlin/Heidelberg. 6th ed.
13. Enzyme Catalysis in Organic Synthesis 2012, vols. 1-3. Wiley-VCH, Weinheim.
14. Stereochemistry and Biological Activity of Drugs 1983, Blackwell, London. E.J. Ariëns, W. Soudíjn, P.B.M.W.M. Timmermans (Eds.).
15. Simonyi M. Med. Res. Rev. 1984, 4:359.
16. Jamali F., Mehvar R., Pasutto F.M. J. Pharm. Sci. 1989, 78:695.
17. Drug Stereochemistry: Analytical Methods and Pharmacology 1993, Dekker, New York. 2nd ed. I.W. Wainer (Ed.).
18. Testa B. Chirality 1989, 1:7.
19. Crossley R. Chirality and the Biological Activity of Drugs 1995, CRC Press, Boca Raton.
20. Eichelbaum M., Gross A.S. Advances in Drug Research 1996, vol. 28:1. Academic Press, London.
21. Chemical Analysis, Vol. 142: The Impact of Stereochemistry on Drug Development and Use 1997, Wiley & Sons, New York.
22. Hutt A.J. Smith and Williams' Introduction to the Principles of Drug Design and Action 1998, 97. Harwood Academic, Amsterdam. H.J. Smith (Ed.).
23. Mori K. Chirality 2011, 23:449.
24. Caldwell J. Chirality 1989, 1:249.
25. Hutt A.J. Chirality 1991, 3:161.
26. F.D.A. statement Chirality 1992, 4:338.
27. Gross M., Cartwright A., Campbell B., Bolton R., Holmes K., Kirkland K., Salmonson T., Robert J.-L. Drug Inf. J. 1993, 27:453.
28. Rauws A.G., Groen K. Chirality 1994, 6:72.
29. Shindo H., Caldwell J. Chirality 1995, 7:349.
30. Branch S.K. Chiral Separation Techniques: A Practical Approach 2001, 317. Wiley-VCH, Weinheim. 2nd ed. G. Subramanian (Ed.).
31. Hutt A.J. Drug Metab. Drug Interact. 2007, 22:79.
32. Bertucci C., Pistolozzi M., De Simone A. Anal. Bioanal. Chem. 2010, 398:155.
33. Bun Ching C., Zhang J., Sui J., Ning Chen W. Proteomics 2010, 10:888.
34. Brooks W.H., Guida W.C., Daniel K.G. Curr. Top. Med. Chem. 2011, 11:760.
35. Salvadori P., Rosini C., Bertucci C. J. Org. Chem. 1984, 49:5050.
36. Salvadori P., Bertucci C., Rosini C. Circular Dichroism: Principles and Applications 1994, 541. VCH Publishers, New York. 1st ed. K. Nakanishi, N. Berova, R.W. Woody (Eds.).
37. Bertucci C., Domenici E., Salvadori P. J. Pharm. Biomed. Anal. 1990, 8:843.
38. Salvadori P., Bertucci C., Rosini C. Chirality 1991, 3:376.
39. Bertucci C., Salvadori P., Lopes Guimarães L.F. J. Chromatogr. A 1994, 666:535.
40. Mannschreck A. Chirality 1992, 4:163.
41. Drake A.F., Gould J.M., Mason S.F. J. Chromatogr. 1980, 202:239.
42. Lloyd D.K., Goodall D.M. Chirality 1989, 1:251.
43. Yeung E.S., Steenhoek L.E., Woodruff S.D., Kuo J.C. Anal. Chem. 1980, 52:1399.
44. Bringmann G., Gulder T.A.M., Reichert M., Gulder T. Chirality 2008, 20:628.
45. Bringmann G., Götz D., Bruhn T. Comprehensive Chiroptical Spectroscopy 2012, vol. 2:355. Wiley & Sons, Hoboken.
46. Zukowski J., Tang Y., Berthod A., Armstrong D.W. Anal. Chim. Acta 1992, 258:83.
47. Gergely A. Analytical Applications of Circular Dichroism 1994, 279. Elsevier, Amsterdam. H.G. Brittain, N. Purdie (Eds.).
48. Lodevico R.G., Bobbitt D.R., Edkins T.J. Talanta 1997, 44:1353.
49. Eliel E.L., Wilen S.H. Stereochemistry of Organic Compounds 1994, Wiley & Sons, New York, pp. 991-1118.
50. Salvadori P., Rosini C., Bertucci C. Chemical Analysis, Vol. 142: The Impact of Stereochemistry on Drug Development and Use 1997, 493. Wiley & Sons, New York.
51. Polavarapu P.L. Chem. Rec. 2007, 7:125.
52. Berova N., Bari L.D., Pescitelli G. Chem. Soc. Rev. 2007, 36:914.
53. Autschbach J. Chirality 2009, 21:E116.
54. Autschbach J., Nitsch-Velasquez L., Rudolph M. Topics in Current Chemistry, Vol. 298: Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures 2011, 1. Springer, Berlin/Heidelberg.
55. Ficarra P., Ficarra R., Bertucci C., Tommasini S., Calabrò M.L., Costantino D., Carulli M. Planta Med. 1995, 61:171.
56. Gaffield W., Waiss A.C. Chem. Commun. (London) 1968, 29.
57. Gaffield W. Tetrahedron 1970, 26:4093.
58. Bertucci C., Andrisano V., Cavrini V., Castiglioni E. Chirality 2000, 12:84.
59. Bossù E., Cotichini V., Gostoli G., Farina A. J. Pharm. Biomed. Anal. 2001, 26:837.
60. Reetz M.T. Angew. Chem. Int. Ed. Engl. 2001, 40:284.
61. Finn M.G. Chirality 2002, 14:534.
62. Mason S.F. Q. Rev. Chem. Soc. 1963, 17:20.
63. Schellman J.A. Chem. Rev. 1975, 75:323.
64. Mason S.F. Molecular Optical Activity and the Chiral Discriminations 1982, Cambridge University Press, Cambridge.
65. Circular Dichroism: Principles and Applications 1994, VCH Publishers, New York. 1st ed. K. Nakanishi, N. Berova, R.W. Woody (Eds.).
66. Circular Dichroism: Principles and Applications 2000, Wiley-VCH, New York. 2nd ed. N. Berova, K. Nakanishi, R.W. Woody (Eds.).
67. Barron L.D. Molecular Light Scattering and Optical Activity 2004, Cambridge University Press, Cambridge.
68. Comprehensive Chiroptical Spectroscopy 2012, vols. 1-2. Wiley & Sons, Hoboken.
69. Fasman G.D. Circular Dichroism and the Conformational Analysis of Biomolecules 1996, Plenum Press, New York.
70. Gottarelli G., Lena S., Masiero S., Pieraccini S., Spada G.P. Chirality 2008, 20:471.
71. Kelly S.M., Jess T.J., Price N.C. Biochim. Biophys. Acta 2005, 1751:119.
72. Whitmore L., Wallace B.A. Biopolymers 2008, 89:392.
73. Bertucci C., Pistolozzi M., De Simone A. Curr. Pharm. Biotechnol. 2011, 12:1508.
74. Kypr J., Kejnovská I., Renčiuk D., Vorlíčková M. Nucleic Acids Res. 2009, 37:1713.
75. Zsila F., Bikadi Z., Fitos I., Simonyi M. Curr. Drug Discov. Technol. 2004, 1:133.
76. Greenfield N.J. Methods Mol. Biol. 2004, 261:55.
77. Krenn W., Verdino P., Uray G., Faber K., Kappe C.O. Chirality 1999, 11:659.
78. Cirilli R., Ferretti R., La Regina G., Morelli G., Pierini M., Piscitelli F., Silvestri R. Talanta 2010, 82:1306.
79. Tedesco D., Zanasi R., Guerrini A., Bertucci C. Chirality 2012, 24:741.
80. Platt J.R. J. Chem. Phys. 1949, 17:484.
81. Mislow K., Glass M.A.W., O'Brien R.E., Rutkin P., Steinberg D.H., Weiss J., Djerassi C. J. Am. Chem. Soc. 1962, 84:1455.
82. Mislow K., Bunnenberg E., Records R., Wellman K., Djerassi C. J. Am. Chem. Soc. 1963, 85:1342.
83. Gawroński J.K. Houben-Weyl Methods of Organic Chemistry, Vol. E21a: Stereoselective Synthesis 1995, 499. Thieme, Stuttgart. G. Helmchen, R. Hoffmann, J. Mulzer, E. Schaumann (Eds.).
84. Gawroński J.K., Grycz P., Kwit M., Rychlewska U. Chemistry 2002, 8:4210.
85. Smith H.E. Chem. Rev. 1998, 98:1709.
86. Moscowitz A., Charney E., Weiss U., Ziffer H. J. Am. Chem. Soc. 1961, 83:4661.
87. Gawroński J.K., Walborsky H.M. Circular Dichroism: Principles and Applications 1994, 301. VCH Publishers, New York. 1st ed. K. Nakanishi, N. Berova, R.W. Woody (Eds.).
88. Salvadori P., Rosini C., Di Bari L. The Chemistry of Dienes and Polyenes 1997, vol. 1:111. Wiley & Sons, New York.
89. Charney E. The Molecular Basis of Optical Activity: Optical Rotatory Dispersion and Circular Dichroism 1979, Wiley & Sons, New York.
90. Kurtán T., Pescitelli G., Salvadori P., Kenéz á., Antus S., Szilágyi L., Illyés T.-z., Szabó I. Chirality 2008, 20:379.
91. Burgstahler A.W., Barkhurst R.C. J. Am. Chem. Soc. 1970, 92:7601.
92. Djerassi C. Optical Rotatory Dispersion: Applications to Organic Chemistry 1960, McGraw-Hill, New York.
93. Moffitt W., Woodward R.B., Moscowitz A., Klyne W., Djerassi C. J. Am. Chem. Soc. 1961, 83:4013.
94. Lightner D.A. Circular Dichroism: Principles and Applications 2000, 261. Wiley-VCH, New York. 2nd ed. N. Berova, K. Nakanishi, R.W. Woody (Eds.).
95. Lightner D.A., Gurst J.E. Organic Conformational Analysis and Stereochemistry from Circular Dichroism Spectroscopy 2000, Wiley-VCH, New York.
96. Rehling H., Jensen H. Tetrahedron Lett. 1972, 13:2793.
97. Ong E.C., Cusachs L.C., Weigang O.E. J. Chem. Phys. 1977, 67:3289.
98. Polonski T., Milewska M.J. Croat. Chim. Acta 1989, 62:129.
99. Galle D., Tolksdorf M., Braun M. Tetrahedron Lett. 1995, 36:4217.
100. Barbaro G., Battaglia A., Guerrini A., Bertucci C. Tetrahedron: Asymmetry 1998, 9:3401.
101. Boyd D.B., Riehl J.P., Richardson F.S. Tetrahedron 1979, 35:1499.
102. Łysek R., Borsuk K., Chmielewski M., Kałuza Z., Urbańczyk-Lipkowska Z., Klimek A., Frelek J. J. Org. Chem. 2002, 67:1472.
103. McCann J., Rauk A., Shustov G.V., Wieser H., Yang D. Appl. Spectrosc. 1996, 50:630.
104. Frelek J., Kowalska P., Masnyk M., Kazimierski A., Korda A., Woźnica M., Chmielewski M., Furche F. Chem. Eur. J. 2007, 13:6732.
105. Gedanken A. The Chemistry of Functional Groups, Supplement E2, Part 1: The Chemistry of Hydroxyl, Ether and Peroxide Groups 1993, 87. Wiley & Sons, New York. S. Patai (Ed.).
106. Michals D.R., Smith H.E. Chirality 1993, 5:20.
107. Beigi F., Bertucci C., Zhu W., Chakir K., Wainer I.W., Xiao R.-P., Abernethy D.R. Chirality 2006, 18:822.
108. Raabe G., Fleischhauer J., Woody R.W. Comprehensive Chiroptical Spectroscopy 2012, vol. 1:543. Wiley & Sons, Hoboken.
109. Berova N., Nakanishi K. Circular Dichroism: Principles and Applications 2000, 337. Wiley-VCH, New York. 2nd ed. N. Berova, K. Nakanishi, R.W. Woody (Eds.).
110. Kasha M., Rawls H.R., Ashraf El-Bayoumi M. Pure Appl. Chem. 1965, 11:371.
111. Mason S.F. Proc. Chem. Soc. 1962, 362.
112. Mason S.F., Vane G.W. J. Chem. Soc. B 1966, 370.
113. Harada N., Nakanishi K. Acc. Chem. Res. 1972, 5:257.
114. Harada N., Nakanishi K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry 1983, University Science Books, Mill Valley.
115. Bellucci G., Berti G., Chiappe C., Lippi A., Marioni F. J. Med. Chem. 1987, 30:768.
116. Pini D., Petri A., Rosini C., Salvadori P., Giorgi R., Di Bugno C., Turbanti L., Marchetti F. Tetrahedron 1994, 50:205.
117. Parish C.A., Dong J.-G., Bornmann W.G., Chang J., Nakanishi K., Berova N. Tetrahedron 1998, 54:15739.
118. Sunazuka T., Shirahata T., Yoshida K., Yamamoto D., Harigaya Y., Nagai T., Kiyohara H., Yamada H., Kuwajima I., ōmura S. Tetrahedron Lett. 2002, 43:1265.
119. Molinski T.F., Brzezinski L.J., Leahy J.W. Tetrahedron: Asymmetry 2002, 13:1013.
120. DeVoe H. J. Chem. Phys. 1964, 41:393.
121. DeVoe H. J. Chem. Phys. 1965, 43:3199.
122. Rosini C., Zandomeneghi M., Salvadori P. Tetrahedron: Asymmetry 1993, 4:545.
123. Salvadori P., Bertucci C., Rosini C., Zandomeneghi M., Gallo G.G., Martinelli E., Ferrari P. J. Am. Chem. Soc. 1981, 103:5553.
124. Rosini C., Bertucci C., Salvadori P., Zandomeneghi M. J. Am. Chem. Soc. 1985, 107:17.
125. Di Bari L., Mannucci S., Pescitelli G., Salvadori P. Chirality 2002, 14:611.
126. Superchi S., Giorgio E., Rosini C. Chirality 2004, 16:422.
127. Bode K.A., Applequist J. J. Am. Chem. Soc. 1998, 120:10938.
128. Rosenfeld L. Z. Phys. 1929, 52:161.
129. Jensen F. Introduction to Computational Chemistry 1999, Wiley & Sons, Chichester.
130. Hansen A.E., Bouman T.D. Advances in Chemical Physics 1980, vol. 44:545. Wiley & Sons, New York.
131. Bouman T.D., Hansen A.E. Croat. Chim. Acta 1989, 62:227.
132. Hansen A.E., Bak K.L. Enantiomer 1999, 4:455.
133. Koslowski A., Sreerama N., Woody R.W. Circular Dichroism: Principles and Applications 2000, 55. Wiley-VCH, New York. 2nd ed. N. Berova, K. Nakanishi, R.W. Woody (Eds.).
134. Sandström J. Chirality 2000, 12:162.
135. Bringmann G., Tasler S., Endress H., Kraus J., Messer K., Wohlfarth M., Lobin W. J. Am. Chem. Soc. 2001, 123:2703.
136. Fugmann B., Arnold S., Steglich W., Fleischhauer J., Repges C., Koslowski A., Raabe G. Eur. J. Org. Chem. 2001, 2001:3097.
137. Harada N. Circular Dichroism: Principles and Applications 2000, 431. Wiley-VCH, New York. 2nd ed. N. Berova, K. Nakanishi, R.W. Woody (Eds.).
138. Charney E. Tetrahedron 1965, 21:3127.
139. Lynden-Bell R.M., Saunders V.P. J. Chem. Soc. A 1967, 2061.
140. Hug W., Wagnière G. Theor. Chim. Acta 1970, 18:57.
141. Brown A., Kemp C.M., Mason S.F. J. Chem. Soc. A 1971, 751.
142. Snatzke G. Angew. Chem. Int. Ed. Engl. 1979, 18:363.
143. Snatzke G., Wynberg H., Feringa B., Marsman B.G., Greydanus B., Pluim H. J. Org. Chem. 1980, 45:4094.
144. Robin M.B., Basch H., Kuebler N.A., Kaplan B.E., Meinwald J. J. Chem. Phys. 1968, 48:5037.
145. Bendazzoli G.L., Gottarelli G., Palmieri P. J. Am. Chem. Soc. 1974, 96:11.
146. Crawford T.D. Comprehensive Chiroptical Spectroscopy 2012, vol. 1:675. Wiley & Sons, Hoboken.
147. Pecul M., Ruud K. Response Theory and Molecular Properties (A Tribute to Jan Linderberg and Poul Jørgensen) 2005, 185. Academic Press, London. H.J.A. Jensen (Ed.).
148. Goerigk L., Kruse H., Grimme S. Comprehensive Chiroptical Spectroscopy 2012, vol. 1:643. Wiley & Sons, Hoboken.
149. Autschbach J. Comprehensive Chiroptical Spectroscopy 2012, vol. 1:593. Wiley & Sons, Hoboken.
150. Bertucci C., Pistolozzi M., Tedesco D., Zanasi R., Ruzziconi R., Di Pietra A.M. J. Chromatogr. A 2012, 1232:128.
151. P.L. Polavarapu, Chirality, in press. doi:10.1002/chir.22015.
152. Stephens P.J., Harada N. Chirality 2010, 22:229.
153. Tomasi J., Mennucci B., Cammi R. Chem. Rev. 2005, 105:2999.
154. Mennucci B., Cappelli C., Cammi R., Tomasi J. Chirality 2011, 23:717.
155. Bringmann G., Messer K., Wohlfarth M., Kraus J., Dumbuya K., Rückert M. Anal. Chem. 1999, 71:2678.
156. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 1969, 34:2543.
157. Monde K., Harada N., Takasugi M., Kutschy P., Suchy M., Dzurilla M. J. Nat. Prod. 2000, 63:1312.
158. Suchý M., Kutschy P., Monde K., Goto H., Harada N., Takasugi M., Dzurilla M., Balentová E. J. Org. Chem. 2001, 66:3940.
159. Diter P., Taudien S., Samuel O., Kagan H.B. J. Org. Chem. 1994, 59:370.
160. Nicoud R.-M., Jaubert J.-N., Rupprecht I., Kinkel J. Chirality 1996, 8:234.
161. Kosugi H., Abe M., Hatsuda R., Uda H., Kato M. Chem. Commun. (Cambridge) 1997, 1997:1857.
162. Rinaldo D., Batista J.M., Rodrigues J., Benfatti A.C., Rodrigues C.M., Dos Santos L.C., Furlan M., Vilegas W. Chirality 2010, 22:726.
163. Bringmann G., Messer K., Saeb W., Peters E.-M., Peters K. Phytochemistry 2001, 56:387.
164. Bringmann G., Messer K., Wolf K., Muhlbacher J., Grune M., Brun R., Louis A.M. Phytochemistry 2002, 60:389.
165. Wu C.-S., Lin Z.-M., Wang L.-N., Guo D.-X., Wang S.-Q., Liu Y.-Q., Yuan H.-Q., Lou H.-X. Bioorg. Med. Chem. Lett. 2011, 21:3261.
166. Batista J.M., Batista A.N.L., Rinaldo D., Vilegas W., Ambrósio D.L., Cicarelli R.M.B., Bolzani V.S., Kato M.J., Nafie L.A., López S.N., Furlan M. J. Nat. Prod. 2011, 74:1154.
167. Bringmann G., Munchbach M., Feineis D., Messer K., Diem S., Herderich M., Clement H.W., Stichel-Gunkel C., Kuhn W. J. Chromatogr. B 2002, 767:321.
168. Sampaio E.P., Hernandez M.O., Carvalho D.S., Sarno E.N. Biomed. Pharmacother. 2002, 56:13.
169. Tseng S., Pak G., Washenik K., Keltz Pomeranz M., Shupack J.L. J. Am. Acad. Dermatol. 1996, 35:969.
170. Marriott J.B., Muller G., Dalgleish A.G. Immunol. Today 1999, 20:538.
171. Stephens T.D., Bunde C.J.W., Fillmore B.J. Biochem. Pharmacol. 2000, 59:1489.
172. Ito T., Ando H., Suzuki T., Ogura T., Hotta K., Imamura Y., Yamaguchi Y., Handa H. Science 2010, 327:1345.
173. Wnendt S., Finkam M., Winter W., Ossig J., Raabe G., Zwingenberger K. Chirality 1996, 8:390.
174. Eriksson T., Björkman S., Roth B., Höglund P. J. Pharm. Pharmacol. 2000, 52:807.
175. Meyring M., Mühlbacher J., Messer K., Kastner-Pustet N., Bringmann G., Mannschreck A., Blaschke G. Anal. Chem. 2002, 74:3726.
176. Gergely A., Szasz G., Szentesi A., Gyimesi-Forras K., Kokosi J., Szegvari D., Veress G. Anal. Bioanal. Chem. 2006, 384:1506.
177. Williams R.C., Edwards J.F., Joshi A.S., Aubry A.F. J. Pharm. Biomed. Anal. 2001, 25:501.
178. Lecoeur-Lorin M., Delépée R., Ribet J.P., Morin P. J. Sep. Sci. 2008, 31:3009.
179. Lecoeur-Lorin M., Delépée R., Adamczyk M., Morin P. J. Chromatogr. A 2008, 1206:123.