Interconversion of stereochemically labile enantiomers (enantiomerization)

Topics in Current Chemistry

Volumn 341, Issue , 2013, Pages 231-269

  Trapp, Oliver ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Activation parameters; Chirality; Computer simulation; Drugs; Dynamic capillary electrophoresis; Dynamic gas chromatography; Dynamic high performance liquid chromatography; Dynamic super critical chromatography; Enantiomerization; Enantioselective chromatography; Interconversion; Kinetics; Stopped flow techniques; Theoretical plate model; Unified equation

Indexed keywords

ALGORITHM; ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL MODEL; CHROMATOGRAPHY; KINETICS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALGORITHMS; CHROMATOGRAPHY; ELECTROPHORESIS, CAPILLARY; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 84896917254     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2013-453     Document Type: Article

References (120)

1. Lambert JB, Takeuchi Y (1992) Cyclic organonitrogen stereodynamics. VCH Publisher Inc., New York
2. Berl V, Huc I, Khoury RG, Krische MJ, Lehn J-M (2000) Interconversion of single and double helices formed from synthetic molecular strands. Nature 407: 720-723
3. Dugave C, Demange L (2003) Cis-trans isomerization of organic molecules and biomolecules: implications and applications. Chem Rev 103: 2475-2532
4. Busenlehner LS, Armstrong RN (2005) Insights into enzyme structure and dynamics elucidated by amide H/D exchange mass spectrometry. Arch Biochem Biophys 433: 34-46
5. Kessler H (1968) Use of nuclear magnetic resonance to detect intramolecular rotations. Angew Chem Int Ed 7: 898
6. Kalinowski H-O, Kessler H (1973) Fast isomerizations about double bonds. Top Stereochem 7: 295-383
7. Binsch G, Kessler H (1980) The kinetic and mechanistic evaluation of NMR spectra. Angew Chem Int Ed 19: 411-494
8. Lehn JM (1970) Nitrogen inversion - experiment and theory. Top Curr Chem 15: 311-377
9. Lambert JB (1971) Pyramidal atomic inversion. Topics Stereochem 6: 19-105
10. Weseloh G, Wolf C, König WA (1995) A new application of capillary zone electrophoresis: determination of energy barriers of configurationally labile chiral compounds. Angew Chem Int Ed 34: 1635-1636
11. Schurig V, Glausch A, Fluck M (1995) On the enantiomerization barrier of atropisomeric 2,20,3,30,4,60-hexachlorobiphenyl (pcb 132). Tetrahedron Asymmetry 6: 2161-2164
12. Reich S, Schurig V (1999) Stopped-flow multidimensional GC - a new method for the determination of enantiomerization barriers. J Microcolumn Sep 11: 475-479
13. Lorenz K, Yashima E, Okamoto Y (1998) Enantiomeric enrichment of stereolabile chiral spiro compounds by dynamic hplc on chiral stationary phases. Angew Chem Int Ed 37: 1922-1925
14. Reich S, Trapp O, Schurig V (2000) Enantioselective stopped-flow multidimensional gas chromatography - determination of the inversion barrier of 1-chloro-2,2-dimethylaziridine. J Chromatogr A 892: 487-498
15. Trapp O, Schurig V (2000) Stereointegrity of Tröger's base: gas-chromatographic determination of the enantiomerization barrier. J Am Chem Soc 122: 1424-1430
16. Schurig V, Bürkle W, Zlatkis A, Poole CF (1979) Quantitative resolution of pyramidal nitrogen invertomers by complexation chromatography. Naturwissenschaften 66: 423-424
17. Schurig V, Bürkle W (1982) Extending the scope of enantiomer resolution by complexation gas chromatography. J Am Chem Soc 104: 7573-7580
18. Bürkle W, Karfunkel H, Schurig V (1984) Dynamic phenomena during enantiomer resolution by complexation gas chromatography. J Chromatogr 288: 1-14
19. Jung M, Schurig V (1992) Determination of enantiomerization barriers by computer simulation of interconversion profiles: enantiomerization of diaziridines during chiral inclusion gas chromatography. J Am Chem Soc 114: 529-534
20. Kostyanovsky RG, Kadorkina GK, Kostyanovsky VR, Schurig V, Trapp O (2000) Pronounced steric hindrance for nitrogen inversion in 1,3,4-oxadiazolidines. Angew Chem Int Ed 39: 2938-2940
21. Kostyanovsky RG, Schurig V, Trapp O, Lyssenko KA, Averkiev BA, Prosyanik AV, Kadorkina GK, Kostyanovsky VR (2002) Chiral 1-alkoxyaziridines: resolution, nitrogen inversion, structure, and diastereomeric transformations. Mendeleev Commun 12: 137-140
22. Trapp O, Trapp G, Kong J, Hahn U, Vögtle F, Schurig V (2002) Probing the stereointegrity of Tröger's base - a dynamic electrokinetic chromatographic study. Chem Eur J 8: 3629-3634
23. Trapp O, Sahraoui L, Hofstadt W, Könen W (2010) The stereodynamics of 1,2-dipropyldiaziridines. Chirality 22: 284-291
24. Trapp O (2010) Chromatographic peak deconvolution of constitutional isomers by multiple reaction monitoring mass spectrometry. J Chromatogr A 1217: 1010-1016
25. Kamuf M, Trapp O (2011) Stereodynamics of tetramezine. Chirality 23: 113-117
26. Lai Y-H, Marriott PJ, Tan B-C (1985) The barrier to rotation in 9,10-bis(2,3-dimethylphenyl) phenanthrene: conformational interconversion observed at high temperatures by means of gas chromatography. Aust J Chem 38: 307-314
27. Gasparrini F, Lunazzi L, Alcaro S, Villani C (1995) Atropisomerism in hindered naphthyl sulfones investigated by dynamic NMR and dynamic HPLC techniques. J Org Chem 60: 5515-5519
28. Wolf C, König WA, Roussel C (1995) Influence of substituents on the rotational energy barrier of atropisomeric biphenyls - studies by polarimetry and dynamic gas chromatography. Liebigs Ann 1995: 781-786
29. Wolf C, König WA, Roussel C (1995) Conversion of a racemate into a single enantiomer in one step by chiral liquid chromatography: studies with rac-2,20-diiodobiphenyl. Chirality 7: 610-611
30. Wolf C, Pirkle WH, Welch CJ, Hochmuth DH, König WA, Chee G-L, Charlton JL (1997) Determination of the enantiomerization barrier of arylnaphthalene ligands by cryogenic subcritical fluid chromatography and computer simulation. J Org Chem 62: 5208-5210
31. Hochmuth DH, König WA (1999) Synthesis. resolution and determination of energy barriers to rotation of atropisomeric, planar-chiral [n]paracyclophanes by dynamic enantioselective gas chromatography and computer simulation. Tetrahedron Asymmetry 10: 1089-1097
32. Scharwächter KP, Hochmuth DH, Dittmann H, König WA (2001) Synthesis, resolution, and investigation of the rotational interconversion process of atropisomeric 1, n-diaza[n] paracyclophanes using cyclodextrin-mediated capillary zone electrophoresis. Chirality 13: 679-690
33. Spivey AC, Charbonneau P, Fekner T, Hochmuth DH, Maddaford A, Malardier-Jugroot C, Redgrave AJ, Whitehead MA (2001) Energy barriers to rotation in axially chiral analogues of 4-(dimethylamino)pyridine. J Org Chem 66: 7394-7401
34. Tobler E, Lämmerhofer M, Mancini G, Lindner W (2001) On-column deracemization of an atropisomeric biphenyl by quinine-based stationary phase and determination of rotational energy barrier by enantioselective stopped-flow HPLC and CEC. Chirality 13: 641-647
35. Maier F, Trapp O (2012) Stationary phase and solvent effects on the stereodynamics of tropos biphep ligands revealed by a novel HPLC technique. Angew Chem Int Ed 51: 2985-2988
36. Rotzler J, Gsellinger H, Neuburger M, Vonlanthen D, Häussinger D, Mayor M (2011) Racemisation dynamics of torsion angle restricted biphenyl push-pull cyclophanes. Org Biomol Chem 9: 86-91
37. Trapp O, Schurig V (2001) Determination of interconversion barriers by dynamic gas chromatography: epimerization of chalcogran. Chem Eur J 7: 1495-1502
38. Cabrera K, Jung M, Fluck M, Schurig V (1996) Determination of enantiomerization barriers by computer simulation of experimental elution profiles obtained by high-performance liquid chromatography on a chiral stationary phase. J Chromatogr A 731: 315-321
39. Schoetz G, Trapp O, Schurig V (1999) Determination of the enantiomerization barrier of chlorthalidone by dynamic electrokinetic chromatography and computer simulation. J Capill Electrophor Microchip Technol 6: 169-175
40. Schoetz G, Trapp O, Schurig V (2000) Determination of the enantiomerization barrier of oxazepam by dynamic micellar electrokinetic chromatography - comparison of experiment and simulation with ChromWin 99. Enantiomer 5: 391-396
41. Schoetz G, Trapp O, Schurig V (2000) Dynamic micellar electrokinetic chromatography - determination of the enantiomerization barrier of oxazepam, temazepam and lorazepam. Anal Chem 72: 2758-2764
42. Schoetz G, Trapp O, Schurig V (2001) Determination of the enantiomerization barrier of thalidomide by dynamic electrokinetic chromatography. Electrophoresis 22: 3185-3190
43. Schoetz G, Trapp O, Schurig V (2001) Determination of the cis-trans isomerization barrier of several l-peptidyl-l-proline dipeptides by dynamic capillary electrophoresis and computer simulation. Electrophoresis 22: 2409-2415
44. Trapp O, Caccamese S, Schmidt C, Böhmer V, Schurig V (2001) Enantiomerization of an inherently chiral resorcarene derivative: determination of the interconversion barrier by computer simulation of the dynamic HPLC experiment. Tetrahedron Asymmetry 12: 1395-1398
45. Wistuba D, Trapp O, Gel-Moreto N, Galensa R, Schurig V (2006) Stereoisomeric separation of flavanones and flavanone-7-o-glycosides by capillary electrophoresis and determination of interconversion barriers. Anal Chem 78: 3424-3433
46. Hinterwirth H, Lämmerhofer M, Preinerstorfer B, Gargano A, Reischl R, Bicker W, Trapp O, Brecker L, Lindner W (2010) Selectivity issues in targeted metabolomics: separation of phosphorylated carbohydrate isomers by mixed-mode hydrophilic interaction/weak anion exchange chromatography. J Sep Sci 33: 3273-3282
47. Veciana J, Crespo MI (1991) Dynamic HPLC, a method for the determination of rate constants, energy barriers and equilibrium constants of dynamic molecular processes. Angew Chem Int Ed 30: 74-77
48. FDA (1992) FDA's policy statement for the development of new stereoisomeric drugs. Chirality 4: 338-340
49. de Camp WH (1989) The FDA perspective on the development of stereoisomers. Chirality 1: 2-6
50. Schurig V (1998) Peak coalescence phenomena in enantioselective chromatography. Chirality 10: 140-146
51. Reist M, Testa B, Carrupt P-A, Jung M, Schurig V (1995) Racemization, enantiomerization, diastereomerization, and epimerization: their meaning and pharmacological significance. Chirality 7: 396-400
52. Schurig V, Jung M, Schleimer M, Klärner F-G (1992) Investigation of the enantiomerization barrier of homofuran by computer simulation of interconversion profiles obtained by complexation gas chromatography. Chem Ber 125: 1301-1303
53. Schurig V, Reich S (1998) Determination of the rotational barriers of atropisomeric polychlorinated biphenyls (PCBs) by a novel stopped-flow multidimensional gas chromatographic technique. Chirality 10: 316-320
54. Martin AJP, Synge RLM (1941) A new form of chromatogram employing two liquid phases. Biochem J 35: 1358-1368
55. Craig LC (1944) Identification of small amounts of organic compounds by distribution studies. J Biol Chem 155: 519-534
56. Bassett DW, Habgood HW (1960) A gas chromatographic study of the catalytic isomerization of cyclopropane. J Phys Chem 64: 769-773
57. Kallen J, Heilbronner E (1960) Das Gas-Chromatogramm einer labilen Verbindung (System a -> b). Helv Chim Acta 43: 489-500
58. Felinger A (2008) Molecular dynamic theories in chromatography. J Chromatogr A 1184: 20-41
59. Lange J, Below E, Thede R (2004) Separate determination of mobile-phase rate constants for reversible reactions. J Liq Chromatogr Relat Technol 27: 715-725
60. D'Acquarica I, Gasparrini F, Pierini M, Villani C, Zappia G (2006) Dynamic HPLC on chiral stationary phases: a powerful tool for the investigation of stereomutation processes. J Sep Sci 29: 1508-1516
61. Oxelbark J, Allenmark S (1999) Barriers to stereoinversion of n-aryl-1,3,2-benzodithiazole 1-oxides studied by dynamic enantioselective liquid chromatography. J Org Chem 64: 1483-1486
62. Trapp O, Schurig V (2001) Chromwin - a computer program for the determination of enantiomerization barriers in dynamic chromatography. Comput Chem 25: 187-195
63. Keller RA, Giddings JC (1960) Multiple zones and spots in chromatography. J Chromatogr 3: 205-220
64. Kramer R (1975) Simultan-Reaktionschromatographie mit reversibler Reaktion erster Ordnung. J Chromatogr 107: 241-252
65. Cremer E, Kramer R (1975) Simultan-Reaktionschromatographie mit reversibler Reaktion erster Ordnung. ii. J Chromatogr 107: 253-263
66. Dondi F, Cavazzini A, Pasti L (2006) Chromatography as Levy stochastic process. J Chromatogr A 1126: 257-267
67. Yau WW (1977) Characterizing skewed chromatographic band broadening. Anal Chem 49: 395-398
68. Barber WE, Carr PW (1981) Graphical method for obtaining retention time and number of theoretical plates from tailed chromatographic peaks. Anal Chem 53: 1939-1942
69. Foley JP, Dorsey JG (1984) A review of the exponentially modified Gaussian (EMG) function: evaluation and subsequent calculation of universal data. J Chromatogr Sci 22: 40-46
70. Lee HK, Li SFY, Marriott PJ (1990) A study on the gas chromatographic column as a chemical reactor. Bull Sing N I Chem 18: 109-114
71. Krupcik J, Oswald P, Spánik I, Májek P, Bajdichová M, Sandra P, Armstrong DW (2000) On the use of a peak deconvolution procedure for the determination of energy barrier to enantiomerization in dynamic chromatography. Analusis 28: 859-863
72. Krupcik J, Mydlova J, Majek P, Simon P, Armstrong DW (2008) Methods for studying reaction kinetics in gas chromatography, exemplified by using the 1-chloro-2,2-dimethylaziridine interconversion reaction. J Chromatogr A 1186: 144-160
73. Krupcik J, Oswald P, Majek P, Sandra P, Armstrong DW (2003) Determination of the interconversion energy barrier of enantiomers by separation methods. J Chromatogr A 1000: 779-800
74. Dubsky P, Tesarová E, Gas B (2004) Dynamics of interconversion of enantiomers in chiral separation systems: a novel approach for determination of all rate constants involved in the interconversion. Electrophoresis 25: 733-743
75. Thede R, Below E, Haberland D, Langer SH (1997) Theoretical treatment of first-order reversible reactions occurring in a chromatographic reactor, on the basis of consecutive reactions. Chromatographia 45: 149-154
76. Trapp O, Schurig V (2001) Approximation function for the direct calculation of rate constants and Gibbs activation energies of enantiomerization of racemic mixtures from chromatographic parameters in dynamic chromatography. J Chromatogr A 911: 167-175
77. Trapp O (2006) Unified equation for access to rate constants of first-order reactions in dynamic and on-column reaction chromatography. Anal Chem 78: 189-198
78. Trapp O (2006) Fast and precise access to enantiomerization rate constants in dynamic chromatography. Chirality 18: 489-497
79. Trapp O (2008) Gas chromatographic high-throughput screening techniques in catalysis. J Chromatogr A 1184: 160-190
80. Trapp O, Weber SK, Bauch S, Bäcker T, Hofstadt W, Spliethoff B (2008) High throughput kinetic study of hydrogenations over palladium nanoparticles - combination of reaction and analysis. Chem Eur J 14: 4657-4666
81. Trapp O, Weber SK, Bauch S, Hofstadt W (2007) High-throughput screening of catalysts by combining reaction and analysis. Angew Chem Int Ed 46: 7307-7310
82. Weber SK, Bremer S, Trapp O (2010) Integration of reaction and separation in a micro capillary column reactor - palladium nanoparticle catalyzed C-C bond forming reactions. J Chem Eng Sci 65: 2410-2416
83. Trapp O, Bremer S, Weber SK (2009) Accessing reaction rate constants in on-column reaction chromatography: an extended unified equation for reaction educts and products with different response factors. Anal Bioanal Chem 395: 1673-1679
84. Trapp O (2008) A novel software tool for high throughput measurements of interconversion barriers: DCXplorer. J Chromatogr B 875: 42-47
85. Marriott PJ, Lai Y-H (1988) Capillary column gas chromatographic method for the study of dynamic intramolecular interconversion behaviour. J Chromatogr 447: 29-41
86. Marriott PJ, Lai Y-H (1986) Isomerization process observed for chromium compounds by using the gas chromatographic reactor. Inorg Chem 25: 3680-3683
87. Trapp O, Schurig V, Kostyanovsky RG (2004) The control of the nitrogen inversion in alkylsubstituted diaziridines. Chem Eur J 10: 951-957
88. Roth WR, Winzer M, Korell M, Wildt H (1995) Konjugativ stabilisierte Trimethylenmethan- Derivate. Geometrieabhängigkeit der Singulett-Triplett- Aufspaltung. Liebigs Ann 897-919
89. Jung M, Fluck M, Schurig V (1994) Enantiomerization of 2,20-diisopropylbiphenyl during chiral inclusion gas chromatography: determination of the rotational energy barrier by computer simulation of dynamic elution profiles. Chirality 6: 510-512
90. Biedermann PU, Schurig V, Agranat I (1997) Enantiomerization of environmentally significant overcrowded polychlorinated biphenyls (PCBs). Chirality 9: 350-353
91. Naruse Y, Watanabe H, Inagaki S (1992) A facile access to chiral allenedicarboxylates by deracemization process. Tetrahedron Asymmetry 3: 603-606
92. Naruse Y, Watanabe H, Ishiyama Y, Yoshida T (1997) Enantiomeric enrichment of allendicarboxylates by a chiral organoeuropium reagent. J Org Chem 62: 3862-3866
93. Schurig V, Keller F, Reich S, Fluck M (1997) Dynamic phenomena involving chiral dimethyl-2,3-pentadienedioate in enantioselective gas chromatography and NMR spectroscopy. Tetrahedron Asymmetry 8: 3475-3480
94. Prelog V, Wieland P (1944)Ü ber die Spaltung der Tröger'schen Base in optische Antipoden, ein Beitrag zur Stereochemie des dreiwertigen Stickstoffs. Helv Chim Acta 27: 1127-1134
95. Gasparrini F, Lunazzi L, Misiti D, Villani C (1995) Organic stereochemistry and conformatiopnal analysis from enantioselective chromatography and dynamic nuclear magnetic resonance measurements. Acc Chem Res 28: 163-170
96. Melander WR, Lin H-J, Jacobson J, Horváth C (1984) Dynamic effect of secondary equilibria in reversed phase chromatography. J Phys Chem 88: 4527-4536
97. Jacobson J, Melander W, Vaisnys G, Horváth C (1984) Kinetic study on cis-trans proline isomerization by high-performance liquid chromatography. J Phys Chem 88: 4536-4542
98. Henderson DE, Horváth C (1986) Low temperature high-performance liquid chromatography of cis-trans proline dipeptides. J Chromatogr A 368: 203-213
99. Ma S, Kálmán F,Kálmán A, Thunecke F, Horváth C (1995) Capillary zone electrophoresis at subzero temperatures. separation of the cis and trans conformers of small peptides. J Chromatogr A 716: 167-182
100. Thunecke F, Kálmán A, Kálmán F,Ma S, Rathore AS, Horváth C (1996) Kinetic study on the cis-trans isomerization of peptidyl-proline dipeptides. J Chromatogr A 744: 259-272
101. Rathore AS, Horváth C (1997) Capillary zone electrophoresis of interconverting cis-trans conformers of peptidyl-proline dipeptides: estimation of the kinetic parameters. Electrophoresis 18: 2935-2943
102. Friebe S, Krauss GJ (1992) High-performance liquid chromatographic separation of cis-trans isomers of proline-containing peptides - separation on cyclodextrin bonded silica. J Chromatogr A 598: 139-142
103. Gebauer S, Friebe S, Scherer G, Gübitz G, Krauss GJ (1998) High-performance liquid chromatography on calixarene-bonded silica gels - separations of cis/trans isomers of proline-containing peptides. J Chromatogr Sci 36: 388-394
104. Krauss GJ, Friebe S, Gebauer S (1998) Cavity supported hplc of cis/trans isomers of prolinecontaining peptides using cyclodextrins and calixarenes. J Protein Chem 17: 515-516
105. Lebl M, Gut V (1983) Calculation of the rate constant of a constant of a reversible reaction from the chromatographic peaks for muramyldipeptide anomers. J Chromatogr 260: 478-482
106. Moriyasu M, Kawanishi K, Kato A, Hashimoto Y, Sugiura M, Sai T (1985) Kinetic studies of fast equilibrium by means of high-performance liquid chromatography. xii. Rate constants and energy barriers of intramolecular carbonyl-nitrogen bond rotation of o-substituted acetanilides. Bull Chem Soc Jpn 58: 3351-3355
107. Stephan B, Zinner H, Kastner F, Mannschreck A (1990) Enantiomers of 2,20- spirobichromenes: energy barrier for thermal racemization during hplc on tribenzoylcellulose. Chimia 10: 336-338
108. Cabrera K, Lubda D (1994) Influence of temperature on chiral high-performance liquid chromatographic separations of oxazepam and prominal on chemically bonded β-cyclodextrin as stationary phase. J Chromatogr A 666: 433-438
109. Friary RJ, Spangler M, Osterman R, Schulman L, Schwerdt JH (1996) Enantiomerization of an atropisomeric drug. Chirality 8: 364-371
110. Gasparrini F, Misiti D, Pierini M, Villani C (1997) Enantiomerization barriers by dynamic HPLC. Stationary phase effects. Tetrahedron Asymmetry 8: 2069-2073
111. Villani C, Pirkle WH (1995) Chromatographic resolution of the interconverting stereoisomers of hindred sulfinyl and sulfonyl naphthalene derivatives. Tetrahedron Asymmetry 6: 27-30
112. Gasparrini F, Lunazzi L, Mazzanti A, Pierini M, Pietrusiwicz KM, Villani C (2000) Comparison of dynamic HPLC and dynamic NMR in the study of conformational stereodynamics: case of the enantiomers of a hindered secondary phosphine oxide. J Am Chem Soc 122: 4776-4780
113. Maier F, Trapp O (2013) The stereodynamics of 5,50-disubstituted BIPHEPs. Chirality 25: 126-132
114. Hochmuth DH (1995) Program package Mimesis 1.1, University of Hamburg
115. Weseloh G, Wolf C, König WA (1996) New technique for the determination of interconversion processes based on capillary zone electrophoresis: studies with axially chiral biphenyls. Chirality 8: 441-445
116. Trapp O, Schoetz G, Schurig V (2001) Determination of enantiomerization barriers by dynamic and stopped flow chromatographic methods. Chirality 13: 403-414
117. Bouabdallah S, Trabelsi H, Ben-Dhia T, Sabbah S, Bouzouita K, Khaddar R (2003) RP-HPLC and NMR study of cis-trans isomerization of enalaprilat. J Pharm Biomed Anal 31: 731-741
118. Trapp O, Trapp G, Schurig V (2004) Determination of the cis-trans isomerization barrier of enalaprilat by dynamic capillary electrophoresis and computer simulation. Electrophoresis 25: 318-323
119. Ledger R, Stellwagen E (2005) The sensitivity of the cis/trans- isomerization of enalapril and enalaprilat to solvent conditions. J Pharm Pharmacol 57: 845-850
120. Trapp O (2005) Direct calculation of interconversion barriers in dynamic chromatography and electrophoresis: isomerization of captopril. Electrophoresis 26: 487-493