Redesigning the mechanism of the lipase-catalysed aminolysis of esters

Tetrahedron Asymmetry

Volumn 17, Issue 8, 2006, Pages 1264-1274

  González Sabín, Javier ^a   Lavandera, Iván ^a   Rebolledo, Francisca ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMPHOLYTE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; LIPASE B; SERINE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; AMINOLYSIS; ARTICLE; CANDIDA ANTARCTICA; CHEMICAL STRUCTURE; ENZYME MECHANISM; MOLECULAR MODEL; PRIORITY JOURNAL;

EID: 33646828010     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.04.021     Document Type: Article

References (70)

1. Um I.-K., Hong J.-Y., and Seok J.-A. J. Org. Chem. 70 (2005) 1438-1444 and references cited therein
2. Bruice T.C., and Mayahi M.F. J. Am. Chem. Soc. 82 (1960) 3067-3071
3. Jencks W.P., and Carriuolo J. J. Am. Chem. Soc. 82 (1960) 675-681
4. Bunnett J.F., and Davis G.T. J. Am. Chem. Soc. 82 (1960) 665-674
5. Alfonso I., and Gotor V. Chem. Soc. Rev. 33 (2004) 201-209
6. van Rantwijk F., and Sheldon R.A. Tetrahedron 60 (2004) 501-519
7. Breuer M., Ditrich K., Habicher T., Hauer B., Keßeler M., Stümer R., and Zelinski T. Angew. Chem., Int. Ed. 43 (2004) 788-824
8. Gotor V. Bioorg. Med. Chem. 7 (1999) 2189-2197
9. Skupinska K.A., McEachern E.J., Baird I.R., Skerlj R.T., and Bridger G.J. J. Org. Chem. 68 (2003) 3546-3551
10. Choi Y.K., Kim M.J., Ahn Y., and Kim M.-J. Org. Lett. 3 (2001) 4099-4101
11. López-Serrano P., Jongejan J.A., Rantwijk F., and Sheldon R.A. Tetrahedron: Asymmetry 12 (2001) 219-228
12. Takayama S., Lee S.T., Hung S.-C., and Wong C.-H. Chem. Commun. (1999) 127-128
13. Messina F., Botta M., Corelli F., and Schneider M.P. J. Org. Chem. 64 (1999) 3767-3769
14. Soledad de Castro M.S., and Sinisterra Gago J.V. Tetrahedron 54 (1998) 2877-2892
15. Öhrner N., Orrenius C., Mattson A., Norin T., and Hult K. Enzyme Microb. Technol. 19 (1996) 328-331
16. Reetz M.T., and Schimossek K. Chimia 50 (1996) 668-669
17. Puertas S., Brieva R., Rebolledo F., and Gotor V. Tetrahedron 49 (1993) 4007-4014
18. Balkenhohl F., Ditrich K., Hauer B., and Ladner W. J. Prakt. Chem. 339 (1997) 381-384
19. Balkenhohl, F.; Hauer, B.; Ladner, W.; Pressler, U. (BASF AG), DE 4332738, 1993; Chem. Abstr.1995, 122, 289035.
20. Ditrich, K.; Balkenhohl, F.; Ladner, W. (BASF AG), DE 19534208, 1995; Chem. Abstr.1997, 126, 277259.
21. Hedstrom L. Chem. Rev. 102 (2002) 4501-4523
22. Fersht A.R. Enzyme Structure and Mechanism. 2nd ed. (1985), Freeman, Nueva York
23. González-Sabín J., Gotor V., and Rebolledo F. Chem. Eur. J. 10 (2004) 5788-5794
24. González-Sabín J., Gotor V., and Rebolledo F. Tetrahedron: Asymmetry 13 (2002) 1315-1320
25. Sánchez V.M., Rebolledo F., and Gotor V. J. Org. Chem. 64 (1999) 1464-1470
26. Alfonso I., Astorga C., Rebolledo F., and Gotor V. Chem. Commun. (1996) 2471-2472
27. Lavandera I., Fernández S., Ferrero M., and Gotor V. J. Org. Chem. 66 (2001) 4079-4082
28. González-Sabín J., Gotor V., and Rebolledo F. Tetrahedron: Asymmetry 15 (2004) 481-488
29. González-Sabín J., Gotor V., and Rebolledo F. Tetrahedron: Asymmetry 16 (2005) 3070-3076
30. Thus, trans-2-phenylcyclopentanamine 1, 'cypenamine' and trans-2-phenylcyclopropanamine 5, 'tranylcypromine' are well-known antidepressants:. McGrath W.R., and Kuhn W.L. Arch. Int. Pharmacodyn. Ther. 172 (1968) 405-413
31. Riley T.N., and Brier C.G. J. Med. Chem. 15 (1972) 1187-1188
32. In addition, cis and trans-isomers of 2-phenylcyclopentanamine and 2-phenylcyclohexanamine 1-4 are building blocks of semi-cyclic amidines with potent hypoglycaemic activity:. Hartmann S., Ullrich S., Hupfer C., and Frahm A.W. Eur. J. Med. Chem. 35 (2000) 377-392
33. Grisar J.M., Claxton G.P., Carr A.A., and Wiech N.L. J. Med. Chem. 16 (1973) 679-683
34. They have also been used as starting materials in the synthesis of sulfonamides potentiators of AMPA receptors, the activity being dependent on the stereochemistry of the stereogenic centres:. Shepherd T.A., Aikins J.A., Bleakman D., Cantrell B.E., Rearick J.P., Simon R.L., Smith E.C.R., Stephenson G.A., and Zimmerman D.M. J. Med. Chem. 45 (2002) 2101-2111
35. Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., and Cuccia L.A. J. Org. Chem. 56 (1991) 2656-2665
36. Similar rates of reaction were observed in the lipase-catalysed transesterification of some cis-2-substituted cyclohexanols but, in contrast with the aminolysis reaction, processes catalysed by CAL-B showed very high enantioselectivities in some cases. For instance, see:. Levy L.M., Lavandera I., and Gotor V. Org. Biomol. Chem. 2 (2004) 2572-2577
37. Levy L.M., Dehli J.R., and Gotor V. Tetrahedron: Asymmetry 14 (2003) 2053-2058
38. Tanikaga R., Matsumoto Y., Sakaguchi M., Koyama Y., and Ono K. Tetrahedron Lett. 44 (2003) 6781-6783
39. Brunet C., Zarevucka M., Wimmer Z., and Legoy M.-D. Enzyme Microb. Technol. 31 (2002) 609-614
40. Forró E., Kanerva L.T., and Fülöp F. Tetrahedron: Asymmetry 9 (1998) 513-520
41. Luna A., Astorga C., Fülöp F., and Gotor V. Tetrahedron: Asymmetry 9 (1998) 4483-4487
42. Lavandera I., Fernández S., Magdalena J., Ferrero M., Kazlauskas R.J., and Gotor V. ChemBioChem 6 (2005) 1381-1390
43. Hult K., and Berglund P. Curr. Opin. Biotechnol. 14 (2003) 395-400
44. Kazlauskas R. Science 293 (2001) 2277-2278
45. Kazlauskas R.J. Curr. Opin. Chem. Biol. 4 (2000) 81-88
46. Hæffner F., and Norin T. Chem. Pharm. Bull. 47 (1999) 591-600
47. Uppenberg J., Öhrner N., Norin M., Hult K., Kleywegt G.J., Patkar S., Waagen V., Anthonsen T., and Jones T.A. Biochemistry 34 (1995) 16838-16851
48. Cornell W.D., Cieplak P., Bayly C.I., and Kollmann P.A. J. Am. Chem. Soc. 115 (1993) 9620-9631
49. Weiner S.J., Kollman P.A., Case D.A., Singh U.C., Ghio C., Alagona G., Profeta S., and Weiner P. J. Am. Chem. Soc. 106 (1984) 765-784
50. Uppenberg J., Patkar S., Bergfors T., and Jones T.A. J. Mol. Biol. 235 (1994) 790-792
51. Uppenberg J., Hansen M.T., Patkar S., and Jones T.A. Structure 2 (1994) 293-308
52. Luić M., Tomić B., Leščić I., Šepac D., Šunjić V., Vitale L., Saenger W., and Kojić-Prodić B. Eur. J. Biochem. 268 (2001) 3964-3973
53. Cygler M., Grochulski P., Kazlauskas R.J., Schrag J.D., Bouthillier F., Rubin B., Serreqi A.N., and Gupta A.K. J. Am. Chem. Soc. 116 (1994) 3180-3186
54. To identify the hydrogen bonds, a donor atom to acceptor atom distance of less than 3.20 Å and a donor atom-hydrogen-acceptor atom angle >120° are required.
55. Adalsteinsson H., and Bruice T.C. J. Am. Chem. Soc. 120 (1998) 3440-3447
56. In a very recent paper, we have already shown that similar zwitterionic species could act as intermediates for lipase-catalysed aminolysis reaction (see Ref. 15).
57. To differentiate between TI-2 and this new TI, we call this TI as zwitterionic since both charges are located in atoms linked to the same carbon atom.
58. ε-H of His224 and the N of the amine.
59. The programme Gaussian 98 was used:. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A.11.3 (2002), Gaussian, Pittsburg, PA
60. A similar trend has been observed with other cyclic compounds:. Levy L.M., and Gotor V. J. Org. Chem. 69 (2004) 2601-2602
61. Forró E., and Fülöp F. Tetrahedron: Asymmetry 10 (1999) 1985-1993
62. Forrö E., Szakonyi Z., and Fülöp F. Tetrahedron: Asymmetry 10 (1999) 4619-4626
63. Forró E., Lundell K., Fülöp F., and Kanerva L.T. Tetrahedron: Asymmetry 8 (1997) 3095-3099
64. Maestro A., Astorga C., and Gotor V. Tetrahedron: Asymmetry 8 (1997) 3153-3159
65. H,H values (10-12 Hz), which are indicative of trans-diaxial arrangements between H-1 and H-2; H-1 and H-6ax; and H-2 and H-3ax.
66. Park S., Forró E., Grewal H., Fülöp F., and Kazlauskas R.J. Adv. Synth. Catal. 345 (2003) 986-995
67. Remaining substrates were obtained as mixtures of the free bases and their acetate salts.
68. To abbreviate, we will call these structures as 'assisted TI-Z'.
69. Note that although bond g has a distance larger than 3.20 Å, the excellent angle interaction makes possible a weak H-bond.
70. H-2,H-3ax is indicative of an axial position for H-2.