The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and theunambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis

Journal of Organic Chemistry

Volumn 74, Issue 19, 2009, Pages 7230-7237

  Hajdok, Szilvia ^a   Conrad, Jürgen ^a   Leutbecher, Heiko ^a   Strobel, Sabine ^b   Schleid, Thomas ^b   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BARBITURIC ACID; CATALYZED REACTIONS; CHEMICAL EQUATIONS; DICARBONYLS; DOMINO REACTIONS; LACCASES; NMR SPECTROSCOPY; PYRIDINONES; REACTION PRODUCTS; SPECTROSCOPIC METHOD; STRUCTURE ELUCIDATION; X-RAY CRYSTAL STRUCTURE ANALYSIS;

NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; REACTION KINETICS; SEMICONDUCTING ORGANIC COMPOUNDS; SPECTROSCOPIC ANALYSIS;

CRYSTAL STRUCTURE;

1,3 DICARBONYL DERIVATIVE; 8,9 DIHYDROXYBENZOFURO[3,2 C]QUINOLIN 6(5H) ONE DERIVATIVE; BARBITURIC ACID DERIVATIVE; BENZOFUROPYRIDINONE DERIVATIVE; BENZOFUROQUINOLINONE DERIVATIVE; CARBONYL DERIVATIVE; CATECHOL DERIVATIVE; COUMARIN DERIVATIVE; LACCASE; PYRIDONE DERIVATIVE; QUINOLONE DERIVATIVE; THIOCOUMARIN DERIVATIVE; THIOCOUMESTAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CRYSTAL STRUCTURE; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

AGARICUS; BARBITURATES; CATALYSIS; CATECHOLS; COUMARINS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; LACCASE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; PYRIDONES; QUINOLONES;

EID: 70349598538     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9011915     Document Type: Article

References (120)

1. (a) Salih, K. S. M.; Ayoub, M. T.; Saadeh, H. A.; Al-Masoudi, N. A.; Mubarak, M. S. Heterocycles 2007, 71, 1577.
2. (b) Wyatt, P. G.; Allen, M. J.; Chilcott, J.; Gardner, C. J.; Livermore, D. G.; Mordaunt, J. E.; Nerozzi, F.; Patel, M.; Perren, M. J.; Weingarten, G. G.; Shabbir, S.; Woollard, P. M.; Zhouc, P. Bioorg. Med. Chem. Lett. 2002, 12, 1405.
3. (c) Buckley, G.; Cooper, N.; Dyke, H.; Galleway, F.; Gowers, L.; Gregory, J. C.; Hannah, D. R.; Haughan, A. F.; Hellewell, P. G.; Kendall, H. J.; Lowe, C.; Maxey, R.; Montana, J. G.; Naylor, R.; Picken, C. L.; Runcie, K. A.; Sabin, V.; Tuladhar, B. R.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2000, 10, 2137.
4. (d) McCallion, G. D. Curr. Org. Chem. 1999, 3, 67.
5. (e) Ecker, G.; Chiba, P.; Hitzler, M.; Schmid, D.; Visser, K.; Cordes, H. P.; Csöllei, J.; Seydel, J. K.; Schaper, K.-J. J. Med. Chem. 1996, 39, 4767.
6. (f) Nagahara, T.; Yokoyama, Y.; Inamura, K.; Katakura, S.; Komoriya, S.; Yamaguchi, H.; Hara, T.; Iwamoto, M. J. Med. Chem. 1994, 37, 1200.
7. (a) Militão, G. C. G.; Pinheiro, S. M.; Dantas, I. N. F.; Pessoa, C.; de Moraes, M. O.; Costa-Lotufo, L. V.; Lima, M. A. S.; Silveira, E. R. Bioorg. Med. Chem. 2007, 15, 6687.
8. (b) da Silva, A. J. M.; Melo, P. A.; Silva, N. M. V.; Brito, F. V.; Buarque, C. D.; de Souza, D. V.; Rodrigues, V. P.; Poças, E. S. C.; Noel, F.; Albuquerque, E. X.; Costa, P. R. R. Bioorg. Med. Chem. Lett. 2001, 11, 283.
9. (c) Xiao, Z.; Waters, N. C.; Woodard, C. L.; Li, Z.; Li, P.-K. Bioorg. Med. Chem. Lett. 2001, 11, 2875.
10. (d) Gaido, K. W.; Leonard, L. S.; Lovell, S.; Gould, J. C.; Babai, D.; Portier, C. J.; Mcdonnell, D. P. Toxicol. Appl. Pharmacol. 1997, 143, 205.
11. (e) Wong, S. M.; Antus, S.; Gottsegen, A.; Fessler, B.; Rao, G. S.; Sonnenbichler, J.; Wagner, H. Arzneim.-Forsch. 1988, 38, 661.
12. (f) Daily, A.; Seligmann, O.; Nonnenmacher, G.; Fessler, B.; Wong, S.-M.; Wagner, H. Planta Med. 1988, 54, 50.
13. For reviews, see: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Curr. Org. Chem. 2006, 10, 1423.
14. (b) Kadieva, M. G.; Oganesyan, É. T. Chem. Heterocycl. Compd. 1997, 33, 1245.
15. (c) Stadlbauer, W.; Kappe, T. Heterocycles 1993, 35, 1425.
16. (d) Donelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol.4, pp 657.
17. (e) Cagniant, P.; Cagniant, D. Adv. Heterocycl. Chem. 1975, 18, 337.
18. (a) Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1491.
19. (b) Yao, T; Yue, D.; Larock, R. C. J. Comb. Chem. 2005, 7, 809.
20. (c) da Silva, A. J. M.; Netto, C. D.; Costa, P. R. R. J. Braz. Chem. Soc. 2004, 15, 979.
21. (d) Miyata, O.; Takeda, N.; Naito, T. Org. Lett. 2004, 6, 1761.
22. (e) Kao, C.-L.; Chern, J.-W. J. Org. Chem. 2002, 67, 6772.
23. (f) Lee, Y. R.; Suk, J. Y.; Kim, B. S. Org. Lett. 2000, 2, 1387.
24. (g) Kraus, G. A.; Zhang, N. J. Org. Chem. 2000, 65, 5644.
25. (h) Stadlbauer, W.; Laschober, R.; Kappe, T. Liebigs Ann. 1990, 531.
26. (i) Singh, R. P.; Singh, D. Heterocycles 1985, 23, 903.
27. (j) Yamaguchi, S.; Yoshimoto, Y.; Murai, R.; Masuda, F.; Yamada, M.; Kawase, Y. J. Heterocycl. Chem. 1984, 21, 737.
28. (k) Kawase, Y.; Yamaguchi, S.; Morita, M.; Uesugi, T. Bull. Chem. Soc. Jpn. 1980, 53, 1057.
29. (a) Tadd, A. C.; Fielding, M. R.; Willis, M. C. Tetrahedron Lett. 2007, 48, 7578.
30. (b) Liang, Y.; Tang, S.; Zhang, X.-D.; Mao, L.-Q.; Xie, Y.-X.; Li, J.-H. Org. Lett. 2006, 8, 3017.
31. (c) Yao, T.; Yue, D.; Larock, R. C. J. Org. Chem. 2005, 70, 9985.
32. (d) Li, C. C.; Xie, Z. X.; Zhang, Y. D.; Chen, J. H.; Yang, Z. J. Org. Chem. 2003, 68, 8500.
33. (e) Hiroya, K; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 2000, 4339.
34. (f) Laschober, R.; Kappe, T. Synthesis 1990, 387.
35. (a) Leutbecher, H.; Hajdok, Sz.; Braunberger, C.; Neumann, M.; Mika, S.; Jürgen, C.; Beifuss, U. Green Chem. 2009, 11, 676.
36. (b) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org. Chem. 2007, 72, 9278.
37. (c) Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337.
38. (d) Davarani, S. S. H.; Shamsipur, M.; Nematollahi, D.; Ramyar, S.; Masoumi, L. Chem. Pharm. Bull. 2007, 55, 1198.
39. (e) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. Adv. Synth. Catal. 2006, 348, 1101.
40. (f) Fakhari, A. R.; Nematollahi, D.; Moghaddam, A. B. Electrochim. Acta 2005, 50, 5322.
41. (g) Chauder, B. A.; Kalinin, A. V.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. 1999, 38, 1435.
42. For reviews, see: (a) Faber, K. Biotransformation in organic chemistry; Springer: Berlin, 2004.
43. (b) Bornscheuer, U. T.; Kazlauskas, R. J. Angew. Chem., Int. Ed. 2004, 43, 6032.
44. (c) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
45. Anastas, P. T.; Warner, J. C. Green Chemistry Theory and Practice; Oxford University Press: Oxford, 1998.
46. (a) Ullrich, R.; Hofrichter, M. Cell. Mol. Life Sci. 2007, 64, 271.
47. (b) Schmid, R. D.; Urlacher, V. Modern Biooxidations. Enzymes, Reactions and Applications; Wiley-VCH: Weinheim, 2007.
48. (c) Bernhardt, R. J. Biotechnol. 2006, 124, 128.
49. (d) Urlacher, V. B.; Eiben, S. Trends Biotechnol. 2006, 24, 324.
50. (e) van Beilen, J. B.; Duetz, W. A.; Schmid, A.; Witholt, B. Trends Biotechnol. 2003, 21, 170.
51. (f) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
52. Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
53. (a) Garcia-Junceda, E. Multi-Step Enzyme Catalysis; Wiley-VCH: Weinheim, 2008.
54. (b) Pellissier, H. Tetrahedron 2008, 64, 1563.
55. (c) Pàmies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247.
56. (d) Glueck, S. M.; Mayer, S. F.; Kroutil, W.; Faber, K. Pure Appl. Chem. 2002, 74, 2253.
57. (a) Morozova, O. V.; Shumakovich, G. P.; Gorbacheva, M. A.; Shleev, S. V.; Yaropolov, A. I. Biochemistry (Moscow, Russ. Fed.) 2007, 72, 1136.
58. (b) Claus, H. Micron 2004, 35, 93.
59. (c) Mayer, A. M.; Staples, R. C. Phytochemistry 2002, 60, 551.
60. (d) Thurston, C. F. Microbiology 1994, 140, 19.
61. (a) Witayakran, S.; Ragauskas, A. J. Adv. Synth. Catal. 2009, 351, 1187.
62. (b) Kunamneni, A.; Camarero, S.; Garcia-Burgos, C.; Plou, F. J.; Ballesteros, A.; Alcalde, M. Microbial Cell Fact. 2008, 7, 32.
63. (c) Xu, F.; Damhus, T.; Danielsen, S; Østergaard, L. H. In Modern Biooxidations. Enzymes, Reactions and Applications; Schmid, R. D., Urlacher, V., Eds.; Wiley-VCH: Weinheim, 2007; p 43.
64. (d) Riva, S. Trends Biotechnol. 2006, 24, 219.
65. (e) Burton, S. G. Curr. Org. Chem. 2003, 7, 1317.
66. (a) Fritz-Langhals, E.; Kunath, B. Tetrahedron Lett. 1998, 39, 5955.
67. (b) Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320.
68. (a) Astolfi, P.; Brandi, P.; Galli, C.; Gentili, P; Gerini, M. F.; Greci, L.; Lanzalunga, O. New J. Chem. 2005, 29, 1308.
69. (b) Fabbrini, M.; Galli, C.; Gentili, P.; Macchitella, D. Tetrahedron Lett. 2001, 42, 7551.
70. (c) Potthast, A.; Rosenau, T.; Chen, C. L; Gratzl, J. S. J. Mol. Catal. A: Chem. 1996, 108, 5.
71. d́ Acunzo, F.; Baiocco, P.; Galli, C. New. J. Chem. 2003, 27, 329.
72. Wells, A.; Teria, M.; Eve, T. Biochem. Soc. Trans. 2006, 34, 304.
73. (a) Kidwai, M.; Poddar, R.; Diwaniyan, S.; Kuhad, R. C. Adv. Synth. Catal. 2009, 351, 589.
74. (b) Ganachaud, C.; Garfagnoli, V.; Tron, T.; Iacazio, G. Tetrahedron Lett. 2008, 49, 2476.
75. (c) Mikolasch, A.; Niedermeyer, T. H. J.; Lalk, M.; Witt, S.; Seefeldt, S.; Hammer, E.; Schauer, F.; Gesell Salazar, M.; Hessel, S.; Jülich, W.-D.; Lindequist, U. Chem. Pharm. Bull. 2007, 55, 412.
76. (d) Mikolasch, A.; Niedermeyer, T. H. J.; Lalk, M.; Witt, S.; Seefeldt, S.; Hammer, E.; Schauer, F.; Gesell, M.; Hessel, S.; Jülich, W.-D.; Lindequist, U. Chem. Pharm. Bull. 2006, 54, 632.
77. (e) Niedermeyer, T. H. J.; Mikolasch, A.; Lalk, M. J. Org. Chem. 2005, 70, 2002.
78. (f) Mikolasch, A.; Hammer, E.; Jonas, U.; Popowski, K.; Stielow, A.; Schauer, F. Tetrahedron 2002, 58, 7589.
79. (g) Eggert, C.; Temp, U.; Dean, J. F. D.; Eriksson, K.-E. L. FEBS Lett. 1995, 376, 202.
80. (a) Leutbecher, H.; Conrad, J.; Klaiber, I.; Beifuss, U. Synlett 2005, 3126.
81. (b) Hajdok, Sz.; Leutbecher, H.; Greiner, G.; Conrad, J.; Beifuss, U. Tetrahedron Lett. 2007, 48, 5073.
82. (a) Witayakran, S.; Ragauskas, A. J. Eur. J. Org. Chem. 2009, 358.
83. (b) Witayakran, S.; Geldbaum, L.; Ragauskas, A. J. Tetrahedron 2007, 63, 10958.
84. (a) Witayakran, S.; Ragauskas, A. J. Green Chem. 2007, 9, 475.
85. (b) Witayakran, S.; Zettili, A.; Ragauskas, A. J. Tetrahedron Lett. 2007, 48, 2983.
86. (a) Tsutsumi, N.; Kawashima, K.; Nagata, H.; Ujiie, A.; Endo, H. Jpn. J. Pharmacol. 1995, 67, 169.
87. (b) Yamada, T.; Saito, N.; Anraku, M.; Imai, T.; Otagiri, M. Pharm. Dev. Technol. 2000, 5 (4), 443.
88. (c) Reddy, B. S.; Darbarwar, M. Indian J. Chem. 1985, 24B, 556.
89. (a) Pandey, G.; Muralikrishna, C.; Bhalerao, U. T. Tetrahedron 1989, 45, 6867.
90. (b) Tabaković, I.; Grujić, Z.; Bejtović, Z. J. Heterocycl. Chem. 1983, 20, 635.
91. Laccase activity (AbL) was determined according to a modified procedure taken from: Felici, M.; Artemi, F.; Luna, M.; Speranza, M. J. Chromatogr. 1985, 320, 435.
92. Land, E. J. J. Chem. Soc., Faraday Trans. 1993, 89, 803. A1.02mMsolution of catechol (0.45 mL) in 0.2Mphosphate buffer (pH=6.0) was diluted with 0.2 M phosphate buffer (2.5 mL, pH=6.0) and treated with a solution of laccase from A. bisporus (AbL) in the same buffer (0.2 mL). The change in absorption was followed via UV spectroscopy (λ=390 nm). 1 U is defined as the amount of the enzyme that catalyzes the conversion of 1 μmol of catechol per minute by pH 6.0 and 25 °C (Nomenclature Committee of the International Union of Biochemistry.
93. Eur. J. Biochem. 1979, 97, 319). The activity of laccase amounted to 3.11 U/mg.
94. (a) Stadlbauer, W.; Fiala, W.; Fischer, M.; Hojas, G. J. Heterocycl. Chem. 2000, 37, 1253.
95. (b) Castillo, S.; Ouadahi, H.; Hérault, V. Bull. Soc. Chim. Fr. 1982, 7-8, 257.
96. (a) Jung, J.-C.; Jung, Y.-J.; Park, O.-S. Synth. Commun. 2001, 31 (8), 1195.
97. (b) Koller, G. Chem. Ber. 1927, 60, 1108.
98. Topolski, M. J. Org. Chem. 1995, 60, 5588.
99. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. 1978, 17, 569.
100. Koschorreck, K.; Richter, S. M.; Swierczek, A.; Beifuss, U.; Schmid, R. D.; Urlacher, V. B. Arch. Biochem. Biophys. 2008, 474, 213.
101. Laccase activity was determined according to a modified procedure taken from: Nicotra, S.; Intra, A.; Ottolina, G.; Riva, S.; Danieli, B. Tetrahedron: Asymmetry 2004, 15, 2927. A 0.91 mM solution of ABTS (0.3 mL) in 0.2 M phosphate buffer (pH = 6.0) was diluted with 0.2 M phosphate buffer (2.6 mL, pH = 6.0) and treated with a solution of laccase from A. bisporus (AbL) in the same buffer (0.1 mL). The change in absorption was followed via UV spectroscopy (λ = 414 nm). For AbL 1 U is defined as the amount of the enzyme that catalyzes the conversion of 1 μmol of ABTS per minute by pH 6.0 and 25 °C. The activity of AbL with ABTS as the substrate amounted to 0.61 U/mg. For TvF 1 U is defined as the amount of the enzyme that catalyzes the conversion of 1 μmol of ABTS per minute by pH 4.38 and 25 °C. For Lccβ 1 U is defined as the amount of the enzyme that catalyzes the conversion of 1 μmol of ABTS per minute by pH 5.0 and 25 °C.
102. (a) Alizadeh, A.; Nematollahi, D.; Hbibi, D.; Hesari, M. Synthesis 2007, 10, 1513.
103. (b) Nematollahi, D.; Goodarzi, H. J. Org. Chem. 2002, 67, 5036.
104. (c) Nematollahi, D.; Goodarzi, H.; Tammari, E. J. Chem. Soc., Perkin Trans. 2 2002, 829.
105. (d) Szanto, D.; Trinidad, P.; Walsh, F. J. Appl. Electrochem. 1998, 28, 251.
106. (e) Azzem, A. M.; Zahran, M.; Hagagg, E. Bull. Chem. Soc. Jpn. 1994, 67, 1390.
107. (a) Lacerda, V. Jr; da Silva, G. V. J.; Tormena, C. F.; Williamson, R. T.; Marquez, B. L. Magn. Reson. Chem. 2007, 45, 82.
108. (b) Williamson, R. T.; Boulanger, A.; Vulpanovici, A.; Roberts, M. A.; Gerwick, W. H. J. Org. Chem. 2002, 67, 7927.
109. (c) Marquez, B. L.; Gerwick, W. H.; Williamson, R. T. Magn. Reson. Chem. 2001, 39, 499.
110. (d) Meissner, A.; Sørensen, O. W. Magn. Reson. Chem. 2001, 39, 49.
111. (e) Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866.
112. (a) Kövér, K. E.; Batta, G.; Fehér, K. J. Magn. Reson. 2006, 181, 89.
113. (b) Williamson, R. T.; Marquez, B. L.; Gerwick, W. H.; Kövér, K. E. Magn. Reson. Chem. 2000, 38, 265.
114. Hansen, P. E. Prog. Nucl. Magn. Reson. Spectrosc. 1981, 14, 175.
115. (a) Bradley, S. A.; Krishnamurthy, K. Magn. Reson. Chem. 2005, 43, 117.
116. (b) Crouch, R.; Boyer, R. D.; Johnson, R.; Krishnamurthy, K. Magn. Reson. Chem. 2004, 42, 301.
117. (a) CCDC-714093 (13f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
118. (b) Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
119. (c) Sheldrick, G. M. SHELXS-97, Programs for X-ray Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
120. (d) Sheldrick, G. M. SHELXL-97, Programs for X-ray Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.