Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

Advanced Synthesis and Catalysis

Volumn 352, Issue 2-3, 2010, Pages 395-406

  Rodríguez Mata, María ^a   García Urdiales, Eduardo ^a   Gotor Fernández, Vicente ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amino acids; Dapoxetine; Enzyme catalysis; Hydrolysis; Lipases; Molecular modelling

Indexed keywords

EID: 77149157223     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900676     Document Type: Article

References (94)

1. D. L. Steer, R. A. Lew, P. Perlmutter, A. I. Smith, M. I. Aguilar, Curr. Med. Chem. 2002, 9, 811-822.
2. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, J. Am. Chem. Soc. 1971, 93, 2325-2327.
3. a) S. J. Haycock-Lewandowski, A. Wilder, J. Ahman, Org. Process Res. Dev. 2008, 12, 1094-1103;
4. b) J. Ahman, M. Birch, S. J. Haycock-Lewandowski, J. Long, A. Wilder, Org. Process Res. Dev. 2008, 12, 1104-1113.
5. a) Enantioselective synthesis of β-amino acids, (Ed.: E. Juaristi), Wiley-VCH, New York, 1997;
6. b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
7. c) N. Sewald, Angew. Chem. 2003, 115, 5972-5973;
8. Angew. Chem. Int. Ed. 2003, 42, 5794-5795;
9. d) D.-Y. Ma, D.-X. Wang, J. Pan, Z.-T. Huang, M.-X. Wang, J. Org. Chem. 2008, 73, 4087-4091;
10. e) B. Wu, W. Szymanski, P. Wietzes, S. deWildeman, G. J. Poelarends, B. L. Feringa, D. B. Janssen, ChemBioChem 2009, 10, 338-344.
11. a) J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347;
12. b) Asymmetric Organic Synthesis with Enzymes, (Eds.: V. Gotor, I. Alfonso, E. García-Urdiales), Wiley-VCH, Weinheim, Germany, 2008;
13. c) N. Ran, L. Zhao, Z. Chen, J. Tao, Green Chem. 2008, 10, 361-372;
14. d) J. M. Woodley, Trends Biotechnol. 2008, 26, 321-327.
15. H. J. Federsel, CHEMTECH 1993, 23, 24-33.
16. a) F. van Rantwijk, M. A. P. J. Hacking, R. A. Sheldon, Monatsh. Chem. 2001, 131, 549-569;
17. b) A. Ghanem, H.-Y. Aboul-Enein, Tetrahedron: Asymmetry 2004, 15, 3331-3351;
18. c) F. van Rantwijk, R. A. Sheldon, Tetrahedron 2004, 60, 501-519;
19. nd edn., Wiley-VCH, Weinheim, Germany, 2006;
20. e) V. Gotor-Fernández, V. Gotor, Curr. Org. Chem. 2006, 10, 1125-1143;
21. f) V. Gotor-Fernández, R. Brieva, V. Gotor, J. Mol. Catal. B: Enzym. 2006, 40, 111-120;
22. g) A. Liljeblad, L. T. Kanerva, Tetrahedron 2006, 62, 5831-5854;
23. h) V. Gotor-Fernández, E. Busto, V. Gotor, Adv. Synth. Catal. 2006, 348, 797-812;
24. i) A. Ghanem, Tetrahedron 2007, 63, 1721-1754;
25. j) V. Gotor-Fernández, V. Gotor, Curr. Opin. Drug Discov. Devel. 2009, 12, 784-797.
26. a) V. M. Sánchez, F. Rebolledo, V. Gotor, Tetrahedron: Asymmetry 1997, 8, 37-40;
27. b) S. Gedey, A. Liljeblad, F. Fülöp, L. T. Kanerva, Tetrahedron: Asymmetry 1999, 10, 2573-2581;
28. c) D. Roche, K. Prasad, O. Repic, Tetrahedron Lett. 1999, 40, 3665-3668;
29. d) S. Gedey, A. Liljeblad, L. Lázár, F. Fülöp, L. T. Kanerva, Tetrahedron: Asymmetry 2001, 12, 105-110;
30. e) M. Solymár, F. Fölöp, L. T. Kanerva, Tetrahedron: Asymmetry 2002, 13, 2383-2388;
31. f) M. Solymár, L. T. Kanerva, F. Fülöp, Tetrahedron: Asymmetry 2004, 15, 1893-1897;
32. g) P. Flores-Sánchez, J. Escalante, E. Castillo, Tetrahedron: Asymmetry 2005, 16, 629-634.
33. a) S. J. Faulconbridge, K. E. Holt, L. G. Sevillano, C. J. Lock, P. D. Tiffin, N. Tremayne, S. Winter, Tetrahedron Lett. 2000, 41, 2679-2681;
34. b) Y.-Y. Liu, W.-Y. Lou, M.-H. Zong, R. Xu, X. Hong, H. Wu, Biocatal. Biotransform. 2005, 23, 89-95;
35. c) H. Gröger, O. May, H. Hüsken, S. Georgeson, K. Drauz, K. Landfester, Angew. Chem. 2006, 118, 1676-1679;
36. Angew. Chem. Int. Ed. 2006, 45, 1645-1648;
37. d) J. Ogawa, J. Mano, S. Shimizu, Appl. Microbiol. Biotechnol. 2006, 70, 663-669;
38. e) E. Forró, F. Fülöp. Chem. Eur. J. 2007, 13, 6397-6401;
39. f) G. Tasnádi, E. Forró, F. Fülöp, Tetrahedron: Asymmetry 2008, 19, 2072-2077;
40. g) J. Mendiola, S. García-Cerrada, O. de Frutos M. L. de La Puente, R. L. Gu, V. V. Khau, Org. Process Res. Dev. 2009, 13, 292-296;
41. h) T. Heck, D. Seebach, S. Osswald, M. K. J. ter Wiel, H.-P. E. Kohler, B. Geueke, ChemBioChem 2009, 10, 1558-1561;
42. i) G. Tasnádi, E. Forró, F. Fülöp, Tetrahedron: Asymmetry 2009, 20, 1771-1777.
43. a) E. Forró, T. Paál, G. Tasnádi, F. Fülöp, Adv. Synth. Catal. 2006, 348, 917-923;
44. b) X.-G. Li, M. Läitie, M. Päiviö, L. T. Kanerva, Tetrahedron: Asymmetry 2007, 18, 1567-1573.
45. General information about dapoxetine can be found in http://www. dapoxetine-online.biz/.
46. a) D. W. Robertson; D. C. Thompson, D. T. Wong, Eur. Pat. Appl. EP 288188 A1 19881026, 1988;
47. b) E. Livni, R. W. Satterlee, R. L. Robey, C. A. Alt, E. E. Van Meter, J. W. Babich, W. J. Wheeler, D. D. O Bannon, J. H. Thrall, Nucl. Med. Biol. 1994, 21, 669-675;
48. c) O. Torre, V. Gotor-Fernández, V. Gotor, Tetrahedron: Asymmetry 2006, 17, 860-866;
49. d) S. A. Siddiqui, K. V. Srinivasan, Tetrahedron: Asymmetry 2007, 18, 2099-2103;
50. e) K. Venkatesan, K. V. Srinivasan, Arkivoc 2008, 16, 302-310;
51. f) P. M. Chincholkar, A. S. Kale, V. K. Gumaste, A. R. A. S. Deshmukh, Tetrahedron 2009, 65, 2605-2609.
52. a) V. A. Soloshonok, N. A. Fokina, A. V. Rybakova, I. P. Shishkina, S. V. Galushko, A. E. Sorochinsky, V. P. Kukhar, M. V. Savchenko, V. K. Švedas, Tetrahedron: Asymmetry 1995, 6, 1601-1610;
53. b) C. Y. K. Tan, D. F. Weaver, Tetrahedron 2002, 58, 7449-7461;
54. c) R. Jiang, H. Chen, S. Cheng, Y. Jin, Q. Wang, X. Sun, Disi Junyi Daxue Xuebao 2004, 25, 688-690.
55. Racemic β-phenylalanine (2a) is commercially available from different commercial sources such as Acros Organics, Aldrich, Fluka, etc., so its chemical synthesis was not attempted.
56. D. Rotticci, F. Hæffner, C. Orrenius, T. Norin, K. Hult, J. Mol. Catal. B: Enzym. 1998, 5, 267-272.
57. a) F. Balkenkohl, B. Hauer, W. Ladner, U. Pressler, Ger. Offen. DE 4332738 A1 19950330, 1995;
58. b) F. Balkenkohl, K. Ditrich, B. Hauer, W. Ladner, J. Prakt. Chem./Chem.-Ztg. 1997, 339, 381-384;
59. c) C. Nuebling, K. Ditrich, C. Dully, Ger. Offen DE 19837745 A1 20000224, 2000;
60. d) J. Gónzalez-Sabin, V. Gotor, F. Rebolledo, Tetrahedron: Asymmetry 2004, 15, 481-488;
61. e) M. Cammemberg, K. Hult, S. Park, ChemBioChem 2006, 7, 1745-1749;
62. f) J. Gónzalez-Sabin, V. Gotor, F. Rebolledo, J. Org. Chem. 2007, 72, 1309-1314;
63. g) M.-J. Kim, W.-H. Kim, K. Han, Y. K. Choi, J. Park, Org. Lett. 2007, 9, 1157-1159;
64. h) I. I. Gill, J. Das, R. N. Patel, Tetrahedron: Asymmetry 2007, 18, 1330-1337;
65. i) M. A. J. Veld, K. Hult, A. R. A. Palmans, E. W. Meijer, Eur. J. Org. Chem. 2007, 5416-5421;
66. j) K. Han, J. Park, M.-J. Kim, J. Org. Chem. 2008, 73, 4302-4304;
67. k) K. Ditrich, Synthesis 2008, 2283-2287.
68. C. S. Chen, Y. Fujimoto, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
69. a) R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656-2665;
70. b) A. Tafi, A. vanAlmsick, F. Corelli, M. Crusco, K. E. Laumen, M. P. Schneider, M. Botta, J. Org. Chem. 2000, 65, 3659-3665.
71. P. Domínguez de María, C. Carboni-Oerlemans, B. Tuin, G. Bargeman, A. van der Meer, R. van Gemert, J. Mol. Catal. B: Enzym. 2005, 37, 36-46, and references cited therein.
72. J. Pleiss, M. Fischer, R. D. Schmid, Chem. Phys. Lipids 1998, 93, 67-80.
73. a) E. Holmberg, K. Hult, Biocatalysis 1992, 5, 289-296;
74. b) S. N. Ahmed, R. J. Kazlauskas, A. H. Morinville, P. Grochulski, J. D. Schrag, M. Cygler, Biocatalysis 1994, 9, 209-225;
75. c) M. Arroyo, J. V. Sinisterra, J. Org. Chem. 1994, 59, 4410-4417;
76. d) P. Berglund, M. Holmquist, H. E. Högberg, K. Hult, Biotechnol. Lett. 1995, 17, 55-60;
77. e) M. Holmquist, F. Hæffner, T. Norin, K. Hult, Protein Sci. 1996, 5, 83-88;
78. f) P. Berglund, M. Holmquist, K. Hult, J. Mol. Catal. B: Enzym. 1998, 5, 283-287;
79. g) E. García-Urdiales, N. Ríos-Lombardía, J. Mangas-Sánchez, V. Gotor-Fernández, V. Gotor, Chem-BioChem 2009, 10, 1830-1838.
80. J. Kraut, Annu. Rev. Biochem. 1977, 46, 331-358.
81. A. Magnusson, K. Hult, M. Holmquist, J. Am. Chem. Soc. 2001, 123, 4354-4355.
82. a) M. K. Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, C. Doebler, A. Spannenberg, W. Maegerlein, H. Hugl, M. Beller, Chem. Eur. J. 2006, 12, 1855-1874;
83. b) S. Hata, M. Iguchi, T. Iwasaka, K.-I. Yamada, K. Tomioka, Org. Lett. 2004, 6, 1721-1723.
84. 1010 Sherbrooke Street West, Suite 910, Montréal, Québec, Canada. http://www.chemcomp.com.
85. J. Wang, P. Cieplak, P. A. Kollman, J. Comput. Chem. 2000, 21, 1049-1074.
86. The dielectric constant of 1,4-dioxane at 20 °C is 2.22: D. R. Lide, CRC Handbook of Chemistry and Physics, Taylor & Francis, Oxfordshire, 2006.
87. M. Laberge, Biochim. Biophys. Acta 1998, 1386, 305-330.
88. W. L. DeLano, The PyMOL molecular graphics system, DeLano Scientific 2002, San Carlos, CA, USA, http://www.pymol.org.
89. a) H. M. Berman, K. Henrick, H. Nakamura, Nat. Struct. Biol. 2003, 10, 980;
90. b) H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucleic Acids Res. 2000, 28, 235-242.
91. J. D. Schrag, Y. Li, M. Cygler, D. Lang, T. Burgdorf, H.-J. Hecht, R. Schmid, D. Schomburg, T. J. Rydel, J. D. Oliver, L. C. Strickland, C. M. Dunaway, S. B. Larson, J. Day, A. McPherson, Structure 1997, 5, 187-202.
92. D. A. Lang, M. L. M. Mannesse, G. H. De Haas, H. M. Verheij, B. W. Dijkstra, Eur. J. Biochem. 1998, 254, 333-340.
93. E. García-Urdiales, E. Busto, N. Ríos-Lombardía, V. Gotor-Fernández, V. Gotor, ChemBioChem 2009, 10, 2875-2883.
94. A. Warshel, G. Naray-Szabo, F. Sussman, J.-K. Hwang, Biochemistry 1989, 28, 3629-3637.