Single enantiomeric β-blockers-The existing technologies

Process Biochemistry

Volumn 45, Issue 10, 2010, Pages 1587-1604

  Agustian, Joni ^a,b   Kamaruddin, Azlina Harun ^a   Bhatia, Subhash ^a  

^a SCHOOL OF PHYSICS   (Malaysia)

^b UNIVERSITY OF LAMPUNG   (Indonesia)

Author keywords

Asymmetric synthesis; Dynamic kinetic resolution; Enzymatic membrane reactors; Racemic resolution; Single enantiomeric blockers

Indexed keywords

ASYMMETRIC SYNTHESIS; DYNAMIC KINETIC RESOLUTION; ENANTIOMERIC EXCESS; ENZYMATIC MEMBRANE REACTORS; ENZYMATIC MEMBRANES; HIGH YIELD; IN-SITU; MEMBRANE-BASED EXTRACTION; OPERATING TEMPERATURE; RACEMIC RESOLUTION; SEPARATION METHODS; SIMULTANEOUS FORMATION; VARIOUS SUBSTRATES; WORLD MARKET;

ACETYLATION; BIOREACTORS; CHIRALITY; ENANTIOMERS; INTERNATIONAL TRADE;

MEMBRANES;

EID: 77956174740     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2010.06.022     Document Type: Review

References (272)

1. Food & Drug Administration FDA's policy statement for the development of new stereoisomeric drugs, 57 Fed. Reg., 22249 1992.
2. McConathy J., Owens M.J. Stereochemistry in drug action. J Clin Psychiatry 2003, 5:70-73.
3. Rekoske J.E. Chiral separations. AIChE J 2001, 47(1):2-5.
4. Okamoto Y., Ikai T. Chiral HPLC for efficient resolution of enantiomers. Chem Soc Rev 2008, 37:2593-2608.
5. Caner H., Groner G., Levy L., Agranat I. Trends in the development of chiral drugs. DDT 2004, 9:105-110.
6. Murakami H. From racemates to single enantiomers-chiral synthetic drugs over the last 20 years. Top Curr Chem 2007, 269:273-299.
7. Kennedy H.L. Current utilisation trends for beta blockers in cardiovascular disease. Am J Med 2001, 110(5A):2S-6S.
8. Mehvar R., Brocks D.R. Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans. J Pharm Pharm Sci 2001, 4(2):185-200.
9. Stoschitzky K., Koshucharova G., Zeiker R., Maier R., Lercher P., Watzinger N., et al. Different effects of propranolol, bisoprolol, carvedilol and doxazosin on heart rate, blood pressure, and plasma concentrations of epinephrine and norepinephrine. J Clin Bas Cardiol 2003, 6:69-72.
10. Agrawal Y.K., Patel R.N. Chiral chromatographic separation of β-blockers. J Chromatogr B 2005, 820:23-31.
11. Bose D.S., Narsaiah A.V. An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution. Bioorg Med Chem 2005, 13:627-630.
12. Hefnawy M.M., Sultan M.A., Al-Shehri M.M. Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products. Anal Chem Insights 2006, 2:13-20.
13. Muthukrishnan M., Garud D.R., Joshi R.R., Joshi R.A. Concise synthesis of β-blockers (S)-metoprolol and (S)-betaxolol using hydrolytic kinetic resolution. Tetrahedron 2007, 63:1872-1876.
14. Hefnawy M.M., Sultan M.A., Al-Shehri M.M. Enantioanalysis of bisoprolol in human plasma with a macrocyclic antibiotic HPLC chiral column using fluorescence detection and solid phase extraction. Chem Pharm Bull 2007, 55(2):227-230.
15. Evangelista S., Gasbin U., Pasini A.F., Stranleri C., Boccioleti V., Cominacini L. Effect of DL-nebivolol, its enantiomers and metabolite on the intracellular production of superoxide and nitric oxide in human endothelial cells. Pharm Res 2007, 56(4):303-309.
16. Zhang D., Li F., Kim D.H., Choi H.J., Hyun M.H. Resolution of β-blockers on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid: unusual temperature effect. J Chromatogr A 2005, 1083:89-95.
17. Petersen P.V., Ekelund J., Olsen L., Ovesen S.V. Chiral separations of βl-blocking drug substances using the Pirkle type α-Burke 1 chiral stationary phase. J Chromatogr A 1997, 757:65-71.
18. Wang X., Ching C.B. Chiral separation and modeling of the three-chiral-center β-blocker drug nadolol by simulated moving bed chromatography. J Chromatogr A 2004, 1035:167-176.
19. Avila R., Ruiz R., Amaro-Gonzales D., Diaz O., Gonzales J.A., Nunez A.J. Increased racemate resolution of propranolol esters by lipase immobilized catalysis. Latin Am Appl Res 2005, 35:307-311.
20. Griffith R.K. Adrenergics and adrenergic-blocking agents. Burger's medicinal chemistry and drug discovery 2003, vol. 6:1-37. John Wiley and Sons Inc, New York. 6th ed.
21. Rippley R.K., Yan K.X., Matthews N.D., Greenberg H.E., Herman G.A., Wagner J.A. Human pharmacokinetics and interconversion of enantiomers of MK-0767, a Dual PPAR α/γ Agonist. J Clin Pharm 2007, 47:323-333.
22. Zhang Y., Hidajat K., Ray A.K. Determination of competitive adsorption isotherm parameters of pindolol enantiomers on α1-acid glycoprotein chiral stationary phase. J Chromatogr A 2006, 1131:176-184.
23. Marti{dotless}nez-Gomez M.A., Marti{dotless}nez-Pla J.J., Sagrado S., Villanueva-Camanas R.M., Medina-Hernandez M.J. Chiral separation of oxprenolol by affinity electrokinetic chromatography-partial filling technique using human serum albumin as chiral selector. J Pharm Biomed Anal 2005, 39:76-81.
24. Sambrook A.M., Small R.C. The treatment of hypertension in pregnancy. Anaesth Intens Care Med 2008, 9(3):128-131.
25. Whitson J.T., Roarty J.D., Vijaya L., Robin A.L., Gross R.D., Landry T.A., et al. Efficacy of brinzolamide and levobetaxolol in pediatric glaucomas: a randomized clinical trial. JAAPOS 2008, 12(3). 239.e1-239.e11.
26. Turner K. Highlights from the Patents. A Review of U.S. Patents in the Field of Organic Process Development Published during January and February 2006. Org Proc Res Dev 2006, 10:381-390.
27. Sharma R., Shastri N., Sadhotra P. β-Blockers as glaucoma therapy. JK Science 2007, 9(1):42-45.
28. Vargas M.G., Heydena Y.V., Maftouh M., Massart D.L. Rapid development of the enantiomeric separation of β-blockers by capillary electrophoresis using an experimental design approach. J Chromatogr A 1999, 855:681-693.
29. Frisman W.H. Beta-adrenergic blockers. Circulation 2003, 107:117-119.
30. Reiter M.J. Cardiovascular drug class specificity: β-blockers. Prog Cardiovasc Dis 2004, 47(1):11-33.
31. Bryan J. Inderal-a forerunner of a radically new generation of products. Pharmacogenomics J 2007, 279:538-539.
32. Stoschitzky K. Melatonin effective therapy for insomnia in beta blocker patients. Reuters Cancer News April 1999; downloaded on 22 January 2008 from http://www.oncolink.com/resources/article.cfm?c=3&s=8&ss=23&id=1812&month=4&year=1999.
33. Cordato D.J., Mather L.E., Herkes G.K. Stereochemistry in clinical medicine: a neurological perspective. J Clin Neurosci 2003, 10(6):649-654.
34. Zhang Y., Hidajat K., Ray A.K. Multi-objective optimization of simulated moving bed and Varicol processes for enantio-separation of racemic pindolol. Sep Purif Technol 2009, 65:311-321.
35. Sheldon R.A. Chirotechnology: industrial synthesis of optically active compounds 1993, Marcell-Dekker, New York, p. 51.
36. Kelly J, Devane J. Methods and compositions for use of (S)-bisoprolol. European Patent EP1446109, 04.08.18.
37. Kamal A., Khanna G.B.R., Krishnaji T., Tekumalla V., Ramu R. New chemoenzymatic pathway for β-adrenergic blocking agents. Tetrahedron: Asymmetry 2005, 16:1485-1494.
38. Stoschitzky K., Zernig G., Lindner W. Racemic beta-blockers-fixed combinations of different drugs. J Clin Bas Cardiol 1998, 1(1):15-19.
39. Stoschitzky K., Klein W., Lindner W. Time to reassess chiral aspects of β-adrenoceptor antagonists. Trends Pharmacol Sci 1997, 18:306-307.
40. Wunsche K., Schwaneberg U., Bornscheuer U.T., Meyer H.H. Chemoenzymatic route to β-blockers via 3-hydroxy esters. Tetrahedron: Asymmetry 1996, 7:2017-2022.
41. Bevinakatti H.S., Banerji A.A. Practical chemoenzymatic synthesis of both enantiomers of propranolol. J Org Chem 1991, 56:5372-5375.
42. Jia X.B., Tong Z.D., Chun S.B., Zhu X.X. Enantioseparation of seven amino alcohols on Teicoplanin chiral column. China J Anal Chem 2007, 35(1):55-60.
43. Nathanson J.A. Stereospecificity of beta adrenergic antagonists: R-enantiomers show increased selectivity for beta-2 receptors in ciliary process. J Pharm Exp Ther 1988, 245(1):94-101.
44. Walle T., Web J.G., Bagwel E.E., Wale U.K., Daniel H.B., Gaffney T.E. Stereoselective delivery and actions of beta receptor antagonist. Biochem Pharmacol 1988, 37:115-124.
45. Gagyi L., Gyeresi A., Kilar F. Role of chemical structure in stereoselective recognition of β-blockers by cyclodextrins in capillary zone electrophoresis. J Biochem Biophys Meth 2007, 70:1268-1275.
46. Stoschitzky K., Egginger G., Zernig G., Kelin W., Lindner W. Stereoselective features of (R)- and (S)-atenolol: clinical pharmacological, pharmacokinetic, and radio ligand binding studies. Chirality 1993, 5:15-19.
47. Hutt A.J. Drug chirality and its pharmacological consequences. Introduction to principles of drugs design and action 2006, 117-183. Taylor and Francis Group, New York. 4th ed. H.J. Smith, H. Williams (Eds.).
48. Haeusler G., Schliep H.J., Schelling P. High beta 1-selectivity and favourable pharmacokinetics as the outstanding properties of bisoprolol. J Cardiovasc Pharmacol 1986, 8(11):S2-S15.
49. Saito M., Kawana J., Ohno T., Kaneko M., Mihara K., Hanada K., et al. Enantioselective and highly sensitive determination of carvedilol in human plasma and whole blood after administration of the racemate using normal-phase high-performance liquid chromatography. J Chromatogr B 2006, 843:73-77.
50. Hawkin D.R. Biotransformations: a survey of the biotransformation of drugs and chemicals in animals 1996, vol. 7. The Royal Society of Chemistry, Cambridge, p. 18, 186.
51. Peter M., Gyeresi A., Fulop F. Liquid chromatographic enantioseparation of β-blocking agents with (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate as chiral derivatizing agent. J Chromatogr A 2001, 910:247-253.
52. Dasbiswas A., Shinde S., Dasbiswas D. S-metoprolol: the 2008 clinical review. J Indian Med Assoc 2008, 106(4):259-262.
53. Pauwels P.J., Gommeren W., Lommen G.V., Janssen P.A., Leysen J.E. The receptor binding profile of the new antihypertensive agent nebivolol and its stereoisomers compared with various beta-adrenergic blockers. Mol Pharmacol 1988, 34:843-851.
54. Fan H.R., Zhang W.G. Stereoselective metabolism and pharmacokinetics of chiral drugs. Asian J Drug Met Pharmacokinet 2005, 5(3):169-178.
55. Jeppsson A.B., Johansson U., Waldeck B. Steric aspects of agonism and antagonism at β-adrenoceptors: experiments with enantiomers of terbutaline and pindolol. Act Pharmacol Toxicol 1984, 54(4):285-291.
56. Walter M., Lemoine H., Kaumann A.J. Stimulant and blocking effects of optical isomers of pindolol on the sinoatrial node and trachea of guinea pig. Role of β-adrenoceptor subtypes in the dissociation between blockade and stimulation. Naunyn-Schmiedeberg's Arch Pharmacol 1984, 327:159-175.
57. Stoschitzky K., Lindner W., Rath M., Leitner C., Uray G., Zernig G., et al. Stereoselective hemodynamic effects of (R)-and (S)-propranolol in man. Naunyn-Schmiedeberg's Arch Pharmacol 1989, 339:474-478.
58. Kulig K., Nowicki P., Malawska B. Influence of the absolute configuration on pharmacological activity of antihypertensive and antiarrhytmic drugs. Polish J Pharmacol 2004, 56:49-508.
59. Advani S.V., Singh B.N. Pharmacodynamic, pharmacokinetic and antiarrhythmic properties of d-sotalol, the dextro-isomer of Sotalol. Drugs 1995, 49:664-679.
60. Hutt A.J., Valentova J. The chiral switch: the development of single enantiomer drgs from racemates. Act Facultatis Pharmaceuticae Universitatis Comenianae 2002, 7-23.
61. Kamal A., Sandbhor M., Shaik A.A. Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol. Bioorg Med Chem Lett 2004, 14:4581-4583.
62. Zelaszczyk D., Kononowicz K.K. Biocatalytic approaches to optically active-blockers. Curr Med Chem 2007, 14:53-65.
63. Wang Z., Ouyang J., Baeyens W.R.G. Recent developments of enantioseparation techniques for adrenergic drugs using liquid chromatography and capillary electrophoresis: a review. J Chromatogr B 2008, 862:1-14.
64. Nguyen L.A., He H., Pham-Huy C. Chiral drugs. An overview. Int J Biomed Sci 2006, 2(2):85-100.
65. Caldwell J. Do single enantiomers have something special to offer?. Hum Psychopharmacol 2001, 16:S67-S71.
66. Ong A.L., Kamaruddin A.H., Bhatia S. Current technologies for the production of (S)-ketoprofen: process perspective. Proc Biochem 2005, 40:3526-3535.
67. Patel R.N. Enzymatic synthesis of chiral intermediates for drug development. Adv Synth Catal 2001, 343(6-7):527-546.
68. Joshi RA, Muthukrisnan M, Garud DR, Borikar SP, Gurjar MK. Process for preparations of S-(-)-betaxolol and salts thereof. US Patent US007,019,172B2, 06.03.28.
69. Joshi RA, Murugan M, Garud DR, Borikar SP, Gurjar MK. S-(-)-1-{4-[2-allyloxy)-ethyl]phenoxy}-3-isopropylaminopropan-2-ol, Process for preparations thereof and Process for preparations of S-(-) Betaxolol. US Patent US006,989,465B1, 06.01.24.
70. Joshi R.A., Garud D.R., Muthukrishnan M., Joshi R.R., Gurjar M.K. A convenient synthesis of the enantiomerically pure β-blocker(S)-betaxolol using hydrolytic kinetic resolution. Tetrahedron: Asymmetry 2005, 16:3802-3806.
71. Zhang J.Y., Liu H.M., Wang X.J., Wang P., Zheng J.X. Application of kinetic resolution using HCS as chiral auxiliary: novel synthesis of β-blockers (S)-betaxolol and (S)-metoprolol. Chirality 2009, 21:745-750.
72. Zhang H., Shao H., Youmei A., Zhang Z. Optimized conditions of enantioseparation of β-blockers by CZE using carboxymethylb-cyclodextrin as chiral selector. Chromatographia 2008, 68(7/8):653-658.
73. Takehira Y, Saragai N, Kitaori K. Process for producing optically active atenolol and intermediate thereof. US Patent US005,130,482A, 92.07.14.
74. Takehira Y, Saragai N, Kitaori K. Process for producing optically active atenolol and intermediate thereof. US Patent US005,223,646A, 93.06.29.
75. Mehta SR, Bhawal BM, Deshpande VH, Gurjar MK. Process for producing atenolol of high optical purity. US Patent US006,982,349B1, 2006.01.03.
76. Kitaori K., Takehira Y., Furukawa Y., Yoshimoto H., Otera J. Convenient preparation of enantiopure atenolol by means of preferential crystallization. Chem Pharm Bull 1998, 46(3):505-507.
77. Kitaori K., Takehira Y., Furukawa Y., Yoshimoto H., Otera J. A practical synthesis of optically active atenolol from chiral epichlorohydrin. Chem Pharm Bull 1997, 45(2):412-414.
78. Kawthekar R.B., Bi W.T., Kim G.J. Synthesis and application of bimetallic chiral [Co(salen)]-type complexes: a new catalytic approach to synthesis of optically pure β-blockers via kinetic resolution of epichlorohydrin. Appl Organometal Chem 2008, 22:583-591.
79. Kawthekar R.B., Kim G.J. Enantioselective synthesis of β-blockers via hydrolytic kinetic resolution of terminal oxiranes by using bimetallic chiral {{2,2'-[Cyclohexane-1,2 diylbis(nitrilomethylidyne)]bis[phenolato]}(2-)}cobalt([Co(salen)])-Type Complexes. Helv Chim Acta 2008, 91:317-332.
80. Bevinakatti H.S., Banerji A.A. Lipase catalysis in organic solvents. Application to the synthesis of (R)- and (S)-atenolol. J Org Chem 1992, 57:6003-6005.
81. Bhushan R., Tanwar S. Direct TLC resolution of atenolol and propranolol into their enantiomers using three different chiral selectors as impregnating reagents. Biomed Chromatogr 2008, 22:1028-1034.
82. Bhushan R., Aora M. Direct enantiomeric resolution of (±)-atenolol, (±)-metoprolol, and (±)-propranolol by impregnated TLC using l-aspartic acid as chiral selector. Biomed Chromatogr 2003, 17:226-230.
83. Kumar P., Naidu V., Gupta P. Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds. Tetrahedron 2007, 63:2745-2785.
84. Damle S.V., Patil P.N., Salunkh M.S. Biotransformation with Rhizopus arrhizus and Geothricum candidum for the preparation of (S)-atenolol and (S)-propranolol. Bioorg Med Chem 2000, 8:2067-2070.
85. Damle S.V., Patil P.N., Salunkhe M.M. Chemoenzymatic synthesis of (R)- and (S)-atenolol and propranolol employing lipase catalysed enantioselective esterification and hydrolysis. Synthetic Commun 1999, 29(22):3855-3862.
86. Hodl H., Krainer A., Holzmüller K., Koidl J., Schmid M.G., Gübitz G. Chiral separation of sympatho mimetics and β-blockers by ligand-exchange CE using Cu(II) complexes of l-tartaric acid and l-threonine as chiral selectors. Electrophoresis 2007, 28:2675-2682.
87. Park H., Lee S., Kang S., Jung Y., Jung S. Enantioseparation using sulfated cyclosophoraoses as a novel chiral additive in capillary electrophoresis. Electrophoresis 2004, 25:2671-2674.
88. Schmid M.G., Lecnik O., Sitte U., Gubitz G. Application of ligand-exchange capillary electrophoresis to the chiral separation of a-hydroxy acids and β-blockers. J Chromatogr A 2000, 875:307-314.
89. Arias R., Jimeónez R.M., Alonso R.M., Teólez M., Arrieta I., Flores P., et al. Determination of the β-blocker atenolol in plasma by capillary zone electrophoresis. J Chromatogr A 2001, 916:297-304.
90. Mertzman M.D., Foley J.P. Temperature effects on chiral microemulsion electrokinetic chromatography employing the chiral surfactant dodecoxy carbonyl valine. J Chromatogr A 2005, 1073:181-189.
91. Aturki Z., Vichi F., Messina A., Sinibaldi M. Indirect resolution of β-blocker agents by reversed-phase capillary electrochromatography. Electrophoresis 2004, 25:607-614.
92. Desiderio C., Aturki Z., Fanali S. Use of vancomycin silica stationery phase in packed capillary Electro chromatography I. Enantiomer separation of basic compounds. Electrophoresis 2001, 22:535-543.
93. Dong X., Dong J., Ou J., Zhu Y., Zou H. Preparation and evaluation of a vancomycin immobilized silica monolith as chiral stationary phase for CEC. Electrophoresis 2007, 28:2606-2612.
94. Rizvi S.A.A., Shamsi S.A. Polymeric alkenoxy amino acid surfactants: I. Highly selective class of molecular micelles for chiral separation of β-blockers. Electrophoresis 2003, 24:2514-2526.
95. Jung S.H., Linh P.T., Lim H.K., Kim K.H., Kang J.S. Enantioselective preparation of metoprolol and its major metabolites. Med Chem Nat Prod 2000, 23(3):226-229.
96. Palmer S, Sidenqvist M. Manufacturing process of metoprolol. US Patent US006,252,113B1, 01.06.26.
97. Palmer S, Sidenqvist M. Manufacturing process of metoprolol. European Patent EP98022426, 98.05.28.
98. Keding BI, Lindqvist BAR, Samuelsson BB. Process for preparing S-metoprolol and intermediate therefore. European Patent EP0339006, 89.04.19.
99. Mehra JK, Choubey A, Srivastava BK, Porwal RK, Gautam P. Process for manufacture of metoprolol and salts thereof. European Patent EP1682081, 05.05.26.
100. Nakazono Y, Omata T, Senda S. New optically active metoprolol tartrate salts, and method of preparing them, and method of preparing optically active metoprolol from the tartrate salts. European Patent EP0487237A1, 92.11.12.
101. Bermudez J.L., del Campo C., Salazar L., Llama EF, Sinisterra JV A new application of Candida antarctica lipase for obtaining natural homochiral BBAs aryloxypropanolamines. Tetrahedron: Asymmetry 1997, 7(9):2485-2488.
102. Lim P.H., Linh P.T., Hong H.C., Kim K.K., Kang J.S. Enantioselective determination of metoprolol and major metabolites in human urine by capillary electrophoresis. J Chromatogr B 2001, 755:259-264.
103. Carlsson E., Wikstrom H., Owens P.K. Validation of a chiral capillary Electrochromatography method for metoprolol on a Teicoplanin stationary phase. Chromatographia 2001, 53:419-424.
104. Inoue K. Method for separating optical isomers. US Patent US006,143,180A, 00.11.07.
105. Aboul-Enein H.Y., Islam M.R. Direct high-performance liquid chromatographic separation of penbutolol enantiomers on a cellulose tris-3,5-dimethylphenyl carbamate chiral stationary phase. Chirality 2004, 1(4):301-304.
106. Narina S.V., Sudalai A. Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines. Tetrahedron 2007, 63:3026-3030.
107. Weinstock L.M., Mulvey D.M., Tull R. Synhtesis of the β-adrenergic blocking agent Timolol from optically active precursors. J Org Chem 1976, 41(9):3121-3124.
108. Varkonyi-Schlovicsko E., Takacs K., Hermecz I. An improved process of separation of R- and S-Timolol. J Hetereocyclic Chem 1997, 34:1065-1066.
109. Schwender C.F., Farber S., Blaum C., Shavel J. Derivatives of 3,4-dihydro-l(2H)-naphthalenone as β-adrenergic blocking agents. 1. Bunolol and related analogs. J Med Chem 1970, 13(4):684-688.
110. Del Corral ASD, Garcia PC, Miguel MDCO. Enantioselective process for the preparation of levobunolol. US Patent US005,426,227A, 95.06.20.
111. Phukan P., Sudalai A. Regioselective alkylation of phenol with cyclopentanol over montmorillonite K10: an efficient synthesis of 1-(2-cyclopentylphenoxy)-3-[(1,1-dimethylethyl)amino]propan-2-ol {(S)-penbutolol}. J Chem Soc Perkin Trans 1999, 1:3015-3018.
112. Ader U., Schneider M.P. Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers III. Optically active chlorohydrin derivatives and their conversion. Tetrahedron: Asymmetry 1992, 3(4):521-524.
113. Klunder J.M., Onami T., Sharpless K.B. Arenesulfonate derivatives of homochiral glycidol: versatile chiral building blocks for organic synthesis. J Org Chem 1989, 54:1295-1304.
114. Kan K., Miyama A., Hamaguchi S., Ohashi T., Watanabe K. Synthesis of (S)-β-blockers from (S)-5-hydroxymethyl-3-tertbutyl-2-oxazolidinone or (S)-5-hydroxymethyl-3-isopropyl-2-oxazolidi none. Agric Biol Chem 1985, 49(1):207-210.
115. Dennis RD, Dolak TM, Kreighbaum WE. Process for resolution of optical isomers. US Patent 4,849,527, 89.07.18.
116. Dennis RD, Dolak TM, Kreighbaum WE. Process for resolution of optical isomers. US Patent 4,463,176, 84.07.31.
117. Sheldon R.A. Chirotechnology: designing economic chiral syntheses. J Chem Tech Biotechnol 1996, 67:1-14.
118. Blaser H.U. Industrial asymmetric catalysis: approaches and results. Rend Fis Acc Lincei 2007, 9(18):281-304.
119. Cho B.T., Kang S.K., Yang W.K. Convenient synthesis of enantiopure β-adrenergic blockers (R)-nifenalol, (R)-denopamine, (R)-dichloroisoproterenol and (R)-pronethalol. Bull Korean Chem Soc 2002, 23:1328-1330.
120. Eshghi H., Yazdi H.P. A facile synthesis of (S)-(-)-propranolol. J Sci Isl Rep Iran 2003, 14(1):17-19.
121. Takahashi H., Sakuraba S., Takeda H., Achiwa K. Highly efficient asymmetric hydrogenation of amino ketone derivatives leading to practical syntheses of (S)-propranolol and related compounds. J Am Chem Soc 1990, 112:5876-5878.
122. Sakuraba S., Takahashi H., Takeda H., Achiwa K. Efficient asymmetric hydrogenation of α-amino ketone derivatives. A highly enantioselective synthesis of phenylephrine, levamisole, carnitine and propranolol. Chem Pharm Bull 1995, 43(5):738-747.
123. Klunder J.M., Ko S.Y., Sharpless K.B. Asymmetric epoxidation of allyl alcohol: efficient routes to homochiral β-adrenergic blocking agents. J Org Chem 1986, 51:3710-3712.
124. Larrow J.F., Schaus S.E., Jacobsen E.N. Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN3. An efficient, catalytic route to 1,2-amino alcohols. J Am Chem Soc 1996, 118:7420-7421.
125. Kitaori K., Furukawa Y., Yoshimoto H., Otera J. CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers. Tetrahedron 1999, 55:14381-14390.
126. Sayyed I.A., Thakur V.V., Nikalje M.D., Dewkar G.K., Kotkar S.P., Sudalai A. Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation. Tetrahedron 2005, 61:2831-2838.
127. Carreño M.C., Hernández-Torres G., Urbano A., Colobert F. Sulfoxide-directed stereocontrolled access to 2H-Chromans: total synthesis of the (S,R,R,R)-enantiomer of the antihypertensive drug Nebivolol. Eur J Org Chem 2008, 2035-2038.
128. Candrasekhar S., Reddy M.V. Enantioselective total synthesis of the antihypertensive agent (S,R,R,R)-nebivolol. Tetrahedron 2000, 56:6339-6344.
129. Johannes C.W., Visser M.S., Weatherhead G.S., Hoveyda A.H. Zr-catalyzed kinetic resolution of allylic ethers and Mo-catalyzed chromene formation in synthesis. Enantioselective total synthesis of the antihypertensive agent (S,R,R,R)-Nebivolol. J Am Chem Soc 1998, 120:8340-8347.
130. Kitaori K., Furukawa Y., Yoshimoto H., Otera J. CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl Nosylate. Tetrahedron Lett 1998, 39:3173-3176.
131. Solladie-Cavallo A., Diep-Vohuule A. A two-step asymmetric synthesis of (R)-monoaryl epoxides using a chiral oxathiane as a recoverable reagent: application to the preparation of (R)-β-Adrenergic compounds. J Org Chem 1995, 60:3494-3498.
132. Kothakonda K.K., Bose D.S. The first enantiomerically pure synthesis of (S)- and (R)-Naftopidil utilizing hydrolytic kinetic resolution of (±)-(α-naphthyl) glycidyl ether. Chem Lett 2004, 33(9):1212-1213.
133. Federsel H.J. Asymmetry on large scale: the roadmap to stereoselective processes. Nat Rev Drug Discov 2005, 4:685-697.
134. Panchgalle S.P., Gore R.G., Chavan S.P., Kalkote U.R. Organocatalytic enantioselective synthesis of β-blockers: (S)-propranolol and (S)-naftopidil. Tetrahedron: Asymmetry 2009, 20:1767-1770.
135. Brodfuehrer P.R., Smith P., Dillon J.L., Vemishetti P. Asymmetric synthesis of the antiarrhythmia agent d-Sotalol. Org Proc Res Dev 1997, 1(2):176-178.
136. Nelson W.L., Wennerstrom J.E., Sankar S.R. Absolute configuration of glycerol derivatives. 3. Synthesis and cupra a circular dichroism spectra of some chiral 3-Aryloxy-1,2-propanediols and 3-Aryloxy-1-amino-2-propanols. J Org Chem 1977, 42(6):1006-1012.
137. Soloviev D.V., Matarrese M., Moresco R.M., Todde S., Bonasera T.A., Sudati F., et al. Asymmetric synthesis and preliminary evaluation of (R)- and (S)-[11C]bisoprolol, a putative β1-selective adrenoceptor radioligand. Neurochem Int 2001, 38:169-180.
138. Veloo R.A., Koomen G.J. Synthesis of enantiomerically pure (S)-(-)-propranolol from sorbitol. Tetrahedron: Asymmetry 1993, 4(12):2401-2404.
139. Kamal A., Rao M. Enzyme catalysed stereoselective synthesis of (S)-propanolamines. Tetrahedron: Asymmetry 1994, 5(10):1881-1882.
140. Pan S.C., List B. New Concepts for Organocatalysis. Ernst Schering foundation symposium proceedings, vol. 2 2008, 1-43.
141. Alexakis A. Why Organocatalysis?. CHIMIA 2007, 61(5):212.
142. Pellissier H. Asymmetric organocatalysis. Tetrahedron 2007, 63:9267-9331.
143. Kaimal T.N.B., Prasad R.B.N., Rao T.C. A practical chemoenzymatic route to (S)-(-)-propranolol. Biotechnol Lett 1992, 14(1):21-26.
144. Iriuchijima S., Kojima N. Asymmetric hydrolysis of (±)-l,3-diacetoxy-3-chloropropane and its related compounds with lipase. Synthesis of optically pure (S)-propranolol. Agric Biol Chem 1982, 46(5):1153-1157.
145. Kapoor M., Anand N., Ahmad K., Koul S., Chimni S.S., Taneja S.C., et al. Synthesis of β-adrenergic blockers (R)-(-)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor. Tetrahedron: Asymmetry 2005, 16:717-725.
146. Moreau S.P., Morisseau C., Baratti J., Zylber J., Archelas A., Furstoss R. Microbiological transformations 37. An enantioconvergent synthesis of the β-blocker (R)-nifenalol using a combined chemoenzymatic approach. Tetrahedron 1997, 53(28):9707-9714.
147. Thakkar N.V., Banerji A.A., Bevinakatti H.S. Chemoenzymatic synthesis of S(-) Practolol. Biotechnol Lett 1995, 17(2):217-218.
148. Gihani M.E.T., Williams J.M.J. Dynamic kinetic resolution. Curr Opin Chem Biol 1999, 3:11-15.
149. Pamies O., Backvall J.E. Dynamic kinetic resolution of β-azido alcohols. An efficient route to chiral aziridines and β-amino alcohols. J Org Chem 2001, 66:4022-4025.
150. Padhi S.K., Titu D., Pandian N.G., Chadha A. Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation. Tetrahedron 2006, 62:5133-5140.
151. Cardus G.J., Carnell A.J., Trauthweinb H., Riermeir T. Microbial deracemisation of N-(1-hydroxy-1-phenylethyl)benzamide. Tetrahedron: Asymmetry 2004, 15:239-243.
152. Yang W., Xu J.H., Xie Y., Xu Y., Zhao G., Lin G.Q. Asymmetric reduction of ketones by employing Rhodotorula sp. AS2. 2241 and synthesis of the β-blocker (R)-nifenalol. Tetrahedron: Asymmetry 2006, 17:1769-1774.
153. Buckland B.C., Robinson D.K., Chartrain M. Biocatalysis for pharmaceuticals status and prospects for a key technology. Metab Eng 2000, 2:42-48.
154. Martinez F., del Campo C., Sinisterra J.V., Llama E.F. Preparation of halohydrin β-blocker precursors using yeast-catalysed reduction. Tetrahedron: Asymmetry 2000, 11:4651-4660.
155. Iriuchijima S., Keiyu A., Kojima N. Asymmetric hydrolysis of (±)-l-acetoxy-2,3-dichloropropane. Agric Biol Chem 1982, 46:1593-1597.
156. Khan F.A., Sudheer C. A chiral pool approach to the synthesis of optically active tetrahalo norbornyl building blocks. Org Lett 2008, 10(14):3029-3032.
157. Brown J.M., Davies S.G. Chemical asymmetric synthesis. Nature 1989, 342:631-636.
158. Nelson W.L., Burke T.R. Absolute configuration of glycerol derivatives. 5. Oxprenolol enantiomers. J Org Chem 1978, 43(19):3641-3645.
159. Wang N.X., Yu A.G., Wang G.X., Zhang X.H., Li Q.S., Li Z. A novel synthesis of (S,R,R,R)-α,α'-(iminobis-(methylene))-bis-(6-fluoro-3H,4H-dihydro-2H-1-benzopyran-2-methanol). Synthesis 2007, 8:1154-1159.
160. Yu A.G., Wang N.X., Xing Y.L., Zhang J.P., Yang Y.X., Wang W.W., et al. A convenient synthesis of 1-[6-fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2 ethanediol and 1-[6-fluoro-(2R)-3H,4H dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol. Synlett 2005, 9:1465-1467.
161. Mai KHX, Patil G, Matier WL. Synthesis of aryloxypropanolamines and arylethanolamines. WIPO Patent WO 87/03584 PCT/US86/02407, 87.06.18.
162. Patil G, Mai KHX, Matier WL. Synthesis of aryloxypropanolamines and arylethanolamines. WIPO Patent WO 87/03583 PCT/US86/02406, 87.06.18.
163. Tsuda Y., Yoshimoto K., Nishikawa T. Practical syntheses of [R]- and [S]-1-alkylamino-3-aryloxy-2-propanols from a single carbohydrate precursor. Chem Pharm Bull 1981, 29(12):3593-3600.
164. Danielewics J.C., Kemp J.E.G. Absolute configuration by asymmetric synthesis of (+)-1-(4-acetamidophenoxy)-3-(isopropylamino)-propan-2-ol (Practolol). J Med Chem 1973, 16(2):168-169.
165. Coulson J.M., Richardson J.F., Backhurst J.R., Harker J.H. Chemical engineering. Particle technology and separation processes 2002, vol. 2. Butterworth-Heinemann, Oxford, 1209 p. 5th ed.
166. Viegas R.M.C., Afonso C.A.M., Crespo J.G., Coelhoso I.M. Modelling of the enantio-selective extraction of propranolol in a biphasic system. Sep Purif Technol 2007, 53:224-234.
167. Pellegrino J.J., Noble R.D. Enhanced transport and liquid membranes in bioseparations. TIBTECH 1990, 8:216.
168. Kemmere M.F., Keurentjes J.T.F. Membranes in chiral separations. Chiral separation techniques: a practical approach, second, completely revised and updated edition 2001, 129-150. Wiley-VCH Verlag GmbH, Weinheim. G. Subramanian (Ed.).
169. Subramanian G. Techniques in preparative chiral separation. Chiral separation techniques: a practical approach, second, completely revised and updated edition 2001, Wiley-VCH Verlag GmbH, 358 p. G. Subramanian (Ed.).
170. Abe Y., Shoji T., Kobayasho M., Qing W., Asai N., Nishizawa H. Enantioselective distribution of amino-alcohols in a liquid-liquid two-phase system containing dialkyl l-tartrate and boric acid. Chem Pharm Bull 1995, 43(2):262-265.
171. Keurentjes J.T.F., Nabuurs L.J.W.M., Vegter E.A. Liquid membrane technology for the separation of racemic mixtures. J Membr Sci 1996, 113:351-360.
172. Viegas R.M.C., Afonso C.A.M., Crespo J.G., Coelhoso I.M. Racemic resolution of propranolol in membrane contactors: modelling and process optimisation. J Membr Sci 2007, 305:203-214.
173. Kloosterman M., Elferink V.H.M., Lersel J.V., Roskam J.H., Meijer E.M., Hulshof L.A., et al. Lipases in the preparation of β-blockers. TIBTECH 1988, 6:251-256.
174. Chiou T.W., Chang C.C., Lai C.T., Tai D.F. Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation. Bioorg Med Chem Lett 1997, 7(4):433-436.
175. Avila-Gonzalez R., Pérez-Gilabert M., García-Carmona F. Lipase-catalyzed preparation of S-propranolol in presence of hydroxypropyl β-cyclodextrins. J Biosci Bioeng 2005, 100(4):423-428.
176. Wankat P.C. Large-scale chromatography. Handbook of separation process technology 1987, 733-759. A Wiley-lnterscience Publication, New York. R.W. Rosseau (Ed.).
177. Schulte M., Strube J. Preparative enantioseparation by simulated moving bed chromatography. J Chromatogr A 2001, 906:399-416.
178. Zhang Y., Hidajat K., Ray A.K. Enantio-separation of racemic pindolol on α1-acid glycoprotein chiral stationary phase by SMB and Varicol. Chem Eng Sci 2007, 62:1364-1375.
179. Wang X., Ching C.B. Chiral separation of β-blocker drug (nadolol) by five-zone simulated moving bed chromatography. Chem Eng Sci 2005, 60:1337-1347.
180. Wang X., Liu Y., Yu H.W., Ching C.B. Chiral Separation of propranolol hydrochloride through an SMB process integrated with crystallization. J Ind Eng Chem 2006, 12(6):868-876.
181. Yashima E., Noguchi J., Okamoto Y. Enantiomer separation with cellulose Tris(3,5-dimethylphenylcarbamate) membrane. Enantioselective adsorption and desorption. Chem Lett 1992, 1959-1962.
182. Yashima E., Noguchi N., Okamoto Y. Continuous and preparative enantio-separation of oxprenolol with cellulose tris(3,5-dimethylphenylcarbamate)-coated belt. Tetrahedron: Asymmetry 1995, 6(8):1889-1890.
183. Ghanem A., Hoenen H., Aboul-Enein H.Y. Application and comparison of immobilized and coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases for the enantioselective separation of β-blockers enantiomers by liquid chromatography. Talanta 2006, 68:602-609.
184. Mistry B., Leslie J.L., Eddington N.D. Enantiomeric separation of metoprolol and α-hydroxymetoprolol by liquid chromatography and fluorescence detection using a chiral stationary phase. J Chromatogr B 2001, 758:153-161.
185. Ceccato A., Hubert P., Crommen J. Direct liquid chromatographic enantioseparation of sotalol and other β-blockers using a α1-acid glycoprotein-based chiral stationary phase. J Chromatogr A 1997, 760:190-203.
186. Ekelund J., Arkens A.V., Bronnum-Hansen K., Fich K., Olsen L., Petersen P.V. Chiral separations of β-blocking drug substances using chiral stationary phases. J Chromatogr A 1995, 708:253-261.
187. Haginaka J., Wakai J., Takahashi K., Yasuda H., Katagi T. Chiral separation of propranolol and its ester derivatives on an ovomucoid-bonded silica: influence of pH, ionic strength and organic modifier on retention, enantioselectivity and enantiomeric elution order. Chromatographia 1990, 29(11/12):587-592.
188. Svensson S, Karlsson A., Gyllenhaal O., Vessman J. Chiral separations of metoprolol and some analogs with carbon dioxide on Chiralcel OD and Chiralpak AD stationary phases. Use of chemometrics. Chromatographia 2000, 51(5/6):283-293.
189. Siret L., Bargmann N., Tambute A., Caude M. Direct enantiomeric separation of β-blockers on ChyRoSine-A by supercritical fluid chromatography: supercritical carbon dioxide as transient in situ derivatizing agent. Chirality 2004, 4(4):252-262.
190. Ruiz-Angel M.J., Carda-Broch S., Berthod A. Ionic liquids versus triethylamine as mobile phase additives in the analysis of β-blockers. J Chromatogr A 2006, 1119:202-208.
191. D'Orazio G., Aturki Z., Cristalli M., Quaglia M.G., Fanali S. Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography. J Chromatogr A 2005, 1081:105-113.
192. Kafkova B., Bosakova Z., Tesarova E., Coufal P. Chiral separation of beta-adrenergic antagonists, profen non-steroidal anti-inflammatory drugs and chlorophenoxypropionic acid herbicides using teicoplanin as the chiral selector in capillary liquid chromatography. J Chromatogr A 2005, 1088:82-93.
193. Bhushan R., Thiongo G.T. Direct enantioseparation of some β-adrenergic blocking agents using impregnated thin-layer chromatography. J Chromatogr B 1998, 708:330-334.
194. Basci N.E., Temizer A., Bozkurt A., Isimer A. Optimization of mobile phase in the separation of β-blockers by HPLC. J Pharm Biomed Anal 1998, 18:745-750.
195. Toyo'oka T., Toriumi M., Ishii Y. Enantioseparation of β-blockers labelled with a chiral fluorescent reagent, R(-)-DBD-PyNCS, by reversed-phase liquid chromatography. J Pharm Biomed Anal 1997, 15:1467-1476.
196. Kim K.H, Lee J.H., Ko M.Y., Hong S.P., Youm J.R. Chiral separation of β-blockers after derivatization with (-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride by gas chromatography. Arch Pharm Res 2001, 24(5):402-406.
197. Vandenbosch C., Massart D.L., Egginger G., Lindner W. Liquid chromatographic methods for the chiral separation of β-adrenergic blocking agents. Trends Anal Chem 1993, 12(4):168-177.
198. Gubitz G., Schmid M.G. Chiral separation by capillary electromigration techniques. J Chromatogr A 2008, 1204:140-156.
199. Gubitz G., Schmid M.G. Advances in chiral separation using capillary electromigration techniques. Electrophoresis 2007, 28:114-126.
200. Kuhn R., Hoffstetter-Kuhn S. Chiral separation by capillary electrophoresis. Chromatographia 1992, 34(9/10):505-512.
201. Gubitz G., Schmid M.G. Chiral separation by chromatographic and electromigration techniques. A review. Biopharm Drug Dispos 2001, 22:291-336.
202. Goel T.V., Nikelly J.G., Simpson R.C., Matuszewski B.K. Chiral separation of labetalol stereoisomers in human plasma by capillary electrophoresis. J Chromatogr A 2004, 1027:213-221.
203. Ren X., Dong Y., Huang A., Sun Y., Sun Z. Separation of the enantiomer of four chiral drugs by neutral cyclodextrin-mediated capillary zone electrophoresis. Chromatographia 1999, 49(7/8):411-414.
204. Ren X.Q., Su X.D., Huang A.J., Sun Y.L., Sun Z.P. Separation of chiral drugs with β-CD phosphate by capillary electrophoresis. Chin. Chem Lett 2000, 11(2):153-156.
205. Denola N.L., Quiming N.Q., Catabay A.P., Saito Y., Jinno K. Optimization of capillary electrophoretic enantioseparation for basic drugs with native β-CD as a chiral selector. Electrophoresis 2006, 27:2367-2375.
206. Tamisier-Karolak S.L., Stenger M.A., Bommart A. Enantioseparation of β-blockers with two chiral senters by capillary electrphoresis using sulphated β-cyclodextrins. Electrophoresis 1999, 20:2656-2663.
207. Perrin C., Heyden Y.V., MAftouh M., Massart D.L. Rapid screening for shiral by short-end injection capillary electrophoresis using highly sulfated cyclodextrins as chiral selectors. Electrophoresis 2001, 22:3203-3215.
208. Yang G., Zhao Y., Li M., Zhu Z., Zhuang Q. Study on chiral resolution of three beta-blockers by affinity electrokinetic chromatography. Talanta 2008, 75:222-226.
209. Gomez M.A.M., Pla J.J.M., Sagrado S., Camanas R.M.V., Hernandez M.J.M. Chiral separation of oxprenolol by affinity electrokinetic chromatography-partial filling technique using human serum albumin as chiral selector. J Pharma Biomed Anal 2005, 39:76-81.
210. Peterson A.G., Ahuja E.S., Foley J.E. Enantiomeric separations of basic pharmaceutical drugs by micellar electrokinetic chromatography using a chiral surfactant, N-dodecoxycarbonylvaline. J Chromatogr B: Biomed Appl 1996, 683:15-28.
211. Rizvi S.A.A., Akbay A., Shamsi S.A. Polymeric alkenoxy amino acid surfactants: II. Chiral separations of β-blockers with multiple stereogenic centers. Electrophoresis 2004, 25:853-860.
212. Walshe M., Garcia E., Howarth J., Smyth M.R., Kelly M.T. Separation of the enantiomers of propranolol by incorporation of molecularly imprinted polymer particles as chiral selectors in capillary electrophoresis. Anal Commun 1997, 34:119-122.
213. Hedeland Y., Haglof J., Beronius P., Petersson C. Effect of alkali metal hydroxides on the enantioseparation of amines using di-O-isopropylidene-keto-L-gulonic acid as the selector in NACE. Electrophoresis 2006, 27:4469-4479.
214. Hedeland Y., Lehtinen J., Pettersson C. Ketopinic acid and diisoproylideneketogulonic acid as chiral ion-pair selectors in capillary electrophoresis Enantiomeric impurity analysis of S-timolol and 1R,2S-ephedrine. J Chromatogr A 2007, 1141:287-294.
215. Carlsson Y., Hedeland M., Bondesson U., Pettersson C. Non-aqueous capillary electrophoretic separation of enantiomeric amines with (2)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid as chiral counter ion. J Chromatogr A 2001, 922:303-311.
216. Joselito P., Quirino J.P., Terabe S. Electrokinetic chromatography. J Chromatogr A 1999, 856:465-482.
217. Pyell U. Theory of electrokinetic chromatography. Electrokinetic chromatography: theory, instrumentation and applications 2006, 3-31. John Wiley & Sons, Ltd., Chichester. U. Pyell (Ed.).
218. Lin C.E., Chen Y.C., Chang C.C., Wang D.Z. Migration behaviour and selectivity of β-blockers in micellar electrokinetic chromatography. Influence of micelle concentration of cationic surfactants. J Chromatogr A 1997, 775:349-357.
219. Schmid M.G., Grobuschek N., Lecnik O., Gubitz G. Chiral ligand-exchange capillary electrophoresis methods. J Biochem Biophys 2001, 48:143-154.
220. Schweitz L., Spégel P., Nilsson S. Molecularly imprinted microparticles for capillary electrochromatographic enantiomer separation of propranolol. Analyst 2000, 125:899-1901.
221. Lin B., Shi Z.G., Hui-Juan Zhang H.J., Ng S.C., Feng Y.Q. Perphenylcarbamoylated-cyclodextrin bonded-silica particles as chiral stationary phase for enantioseparation by pressure assisted capillary electrochromatography. Electrophoresis 2006, 27:3057-3065.
222. Schweitz L., Andersson L.I., Nilsson S. Molecularly imprinted CEC sorbents: investigations into polymer preparation and electrolyte composition. Analyst 2002, 127:22-28.
223. Otsuka K., Mikami C., Terabe S. Enantiomer separations by capillary electrochromatography using chiral stationary phases. J Chromatogr A 2000, 887:457-463.
224. Koide T., Ueno K. Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with monolithic chiral stationary phases of b-cyclodextrin-bonded negatively charged polyacrylamide gels. J Chromatogr A 2000, 893:177-187.
225. Ager D.J. Introduction. Handbook of chiral chemicals 1999, 1-8. Marcell-Dekker, New York. D.J. Ager (Ed.).
226. Fogassy E., Nogradi N., Kozma D., Egri E., Palovics E., Kiss V. Optical resolution methods. Org Biomol Chem 2006, 4:3011-3030.
227. Viegas R.M.C., Crespo J.G., Coelhoso I.M. Hybrid modelling of the racemic resolution of propranolol in membrane contactors. Desalination 2006, 200:595-597.
228. Wang N.X., Tang X.L. An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropyl amino-propoxy)phenyl]-butanamide with high enantioselectivity. Sci China Ser B-Chem 2009, 52(8):1216-1219.
229. Ohkuma T., Kitamura M., Noyori R. Ligand design for catalytic asymmetric reduction. New frontiers in asymmetric catalysis 2007, 1-28. John Wiley and Sons Inc., Hoboken. K. Mikami, M. Lautens (Eds.).
230. Kamaruddin A.H., Uzir M.H., Aboul-Enein H., Halim H.N.A. Chemoenzymatic and Microbial dynamic kinetic resolutions. Chirality 2008, 21(4):449-467.
231. Mordant C., de Andrade C.C., Touati R., Ratovelomanana-Vidal V., Hassine B.B., Genet J.P. Stereoselective synthesis of Diltiazem via dynamic kinetic resolution. Synthesis 2003, 15:2405-2409.
232. Johnston E.V., Bogar K., Backvall J.E. Enantioselective synthesis of (R)-bufuralol via dynamic kinetic resolution in the key step. J Org Chem 2010.
233. Pamies O., Backvall J.E. Combination of enzymes and metal catalysts. A powerful approach in asymmetric catalysis. Chem Rev 2003, 103:3247-3261.
234. Kamal A., Azhar M.A., Krishnaji T., Malik M.S., Azeeza S. Approaches based on enzyme mediated kinetic to dynamic kinetic resolutions: a versatile route for chiral intermediates. Coord Chem Rev 2008, 252:569-592.
235. Gumi T., Ferreira Q., Viegas R.M.C., Crespo J.G., Coelhoso I.M., Palet C. Enantioselective separation of propranolol by chiral activated membranes. Sep Sci Technol 2005, 40(4):773-789.
236. Coelhoso I.M., Cardoso M.M., Viegas R.M.C., Crespo J.P.S.G. Transport mechanisms and modelling in liquid membrane contactors. Sep Purif Technol 2000, 19:183-197.
237. Scriba G.K.E. Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: an update. Electrophoresis 2003, 24:2409-2421.
238. Srinivas N.R., Igwemezie L.N. Chiral separation by high performance liquid chromatography. I. Review on indirect separation of enantiomer as diastereomeric derivatives using ultraviolet, fluorescence and electrochemical detection. Biomed Chromatogr 1991, 6:163-167.
239. To J.G., To N.G., Shao G., Ito M., Nakamura S., Nambara T. Fluorescence chiral derivatization reagents for high liquid chromatographic resolution of enantiomeric hydroxyl compounds) performance. Anal Sci 1990, 6:261-264.
240. Kleidernigg O.P., Maier N.M., Uray G., Lindner W. The chemical and thermal stability of the acetamido group of (R)- and (S)-Atenolol: synthetic and chromatographic studies. Chirality 1994, 6(5):411-419.
241. Giorno L., D'Amore E., Mazzei R., Piacentini E., Zhang J., Drioli E., et al. An innovative approach to improve the performance of two separate phase enzyme membrane reactor by immobilizing lipase in presence of emulsion. J Membr Sci 2007, 295:95-101.
242. Wang Y., Hu Y., Xu J., Luo G., Dai Y. Immobilization of lipase with a special microstructure in composite hydrophilic CA/hydrophobic PTFE membrane for the chiral separation of racemic ibuprofen. J Membr Sci 2007, 293:133-141.
243. Giorno L., Molinari R., Drioli E., Bianchi D., Cesti P. Performance of a biphasic organic/aqueous hollow fibre reactor using immobilized lipase. J Chem Tech Biotechnol 1995, 64:345-352.
244. Ferraz H.C., Alves T.L.M., Borges C.P. Biocatalytic membrane reactor with continuous removal of organic acids by electrodialysis. New insights into membrane science and technology: polymeric and biofunctional membranes 2003, 241-261. Elsevier Science BV, Amsterdam. D. Bhattacharyya, D.A. Butterfield (Eds.).
245. Anand N., Kapoor M., Ahmad K., Koul S., Parshad R., Manhas K.S., et al. Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains. Tetrahedron: Asymmetry 2007, 18:1059-1069.
246. Giorno L., Drioli E. Biocatalytic membrane reactors: applications and perspectives. TIBTECH 2000, 18:339-349.
247. Quan J., Wang N., Cai X.Q., Wu Q., Lin X.F. Controllable selective enzymatic synthesis of N-acyl and O-acylpropranololvinyl esters and preparation of polymeric prodrug of propranolol. J Mol Catal B 2007, 44:1-7.
248. Ghanem A., Schurig V. Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol. Tetrahedron: Asymmetry 2003, 14:57-62.
249. Patel R.N., Banerjee A., Nanduri V., Goswami A., Comezoglu F.T. Enzymatic resolution of racemic secondary alcohols by lipase B from Candida antarctica. JAOCS 2000, 77(10):1015-1019.
250. Högberg H.E., Lindmark M., Isaksson D., Sjödin K., Franssen M.C.R., Jongejan H., et al. Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols. Tetrahedron Lett 2000, 41:3193-3196.
251. Pchelka B.K., Loupy A., Plenkiewicz J., Blanco L. Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation. Tetrahedron: Asymmetry 2000, 11:2719-2732.
252. Ziegler T., Jurisch C. Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof. Tetrahedron: Asymmetry 2000, 11:3403-3418.
253. Panzavolta F., Soro S., D'Amato R., Palocci C., Cernia E., Russo M.V. Acetylenic polymers as new immobilization matrices for lipolytic enzymes. J Mol Catal B 2005, 32:67-76.
254. Paizs C., Tos M., Bodai V., Szaka G., Kmecz I., Simandi B., et al. Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions. Tetrahedron: Asymmetry 2003, 14:1943-1949.
255. Urdiales E.G., Rebolledo F., Go V. Study of the enantioselectivity of the CAL-B-catalysed transesterification of α-substituted α-propylmethanols and α-substituted benzyl alcohols. Tetrahedron: Asymmetry 2001, 12:3047-3052.
256. Cattani M., Bassalo J.M.F. Racemisation, chiral stability and weak interactions. J Quant Spectrosc Rad Transf 2006, 102:441-449.
257. Liljeblad A., Kiviniemi A., Kanerva L.T. Aldehyde-based racemization in the dynamic kinetic resolution of N-heterocyclic a-amino esters using Candida antarctica lipase A. Tetrahedron 2004, 60:671-677.
258. Dinh P.M., Williams J.M.J. Selective racemisation of esters: relevance to enzymatic hydrolysis reactions. Tetrahedron Lett 1999, 40:749-752.
259. Jones M.M., Williams J.M.J. Dynamic kinetic resolution in the hydrolysis of an α-bromo ester. Chem Comm 1998, 2519-2520.
260. Takac S., Bakkal M. Impressive effect of immobilization conditions on the catalytic activity and enantioselectivity of Candida rugosa lipase toward S-Naproxen production. Proc Biochem 2007, 42:1021-1027.
261. Brady D., Steenkamp L., Skein E., Chaplin J.A., Reddy S. Optimisation of the enantioselective biocatalytic hydrolysis of naproxen ethyl ester using ChiroCLEC-CR. Enzyme Microb Technol 2004, 34:283-291.
262. Mori S., Yumoto H., Matsumi R., Nishigaki T., Ebaraa Y., Uejia S. A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive. Tetrahedron: Asymmetry 2005, 16:3698-3702.
263. Madhav M.V., Ching C.B. Study on the enzymatic hydrolysis of racemic methyl ibuprofen ester. J Chem Technol Biotechnol 2001, 76:941-948.
264. Kim M.J., Chung Y.I., Choi Y.K., Lee H.K., Kim D., Park J. (S)-Selective dynamic kinetic resolution of secondary alcohols by the combination of subtilisin and an aminocyclopentadienylruthenium complex as the catalysts. J Am Chem Soc 2003, 125:11494-11495.
265. Liu Y.Y., Xu J.H., Hu Y. Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester. J Mol Catal B 2000, 10:523-529.
266. Nieto I., Rocchietti S., Ubiali D., Speranza G., Morelli C.F., Fuentes I.E., et al. Immobilization of different protein fractions from Rhizomucor miehei lipase crude extract: enzymatic resolution of (R,S)-2-tetralol. Enzyme Microb Technol 2005, 37:514-520.
267. Palomo J.M., Lorente G.F., Mateo C., Ortiz C., Lafuente R.F., Guisan J.M. Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters. Enzyme Microb Technol 2002, 31:775-783.
268. Long W.S., Kamaruddin A.H., Bhatia S. Chiral resolution of racemic ibuprofen ester in an enzymatic membrane reactor. J Membr Sci 2005, 247:185-200.
269. Sakaki K., Hara S., Itoh N. Optical resolution of racemic 2-hydroxy octanoic acid using biphasic enzyme membrane reactor. Desalination 2002, 149:247-252.
270. Giorno L., Li N., Drioli E. Preparation of oil-in-water emulsions using polyamide 10kDa hollow fiber membrane. J Membr Sci 2003, 217:173-180.
271. Bouwer S.T., Cuperus F.P., Derksen J.T.P. The performance of enzyme-membrane reactors. Enzyme Microb Technol 1997, 21:291-296.
272. Deng H.T., Xua Z.K., Dai Z.W., Wu J., Seta P. Immobilization of Candida rugosa lipase on polypropylene microfiltration membrane modified by glycopolymer: hydrolysis of olive oil in biphasic bioreactor. Enzyme Microb Technol 2005, 36:996-1002.