Biocatalytic Synthesis of Highly Enantiopure 1,4-Benzodioxane-2-carboxylic Acid and Amide
Jun Liu
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDe-Xian Wang
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorQi-Yu Zheng
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorJun Liu
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDe-Xian Wang
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorQi-Yu Zheng
Beijing National Laboratory for Molecular Sciences, Laboratory for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorAbstract
Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase and amidase containing microbial whole-cell catalyst, at 10 °C and with the use of methanol as a co-solvent, nitrile and amide biotransformations produce 2S-1,4-benzodioxane-2-carboxamide and 2R-1,4-benzodioxane-2-carboxylic acid in high yields with excellent enantioselectivity.
REFERENCES
- 1a Iwata, H.; Baba, A.; Matsuda, T.; Egawa, M.; Tobe, A.; Saito, K., 1991. EP446921, A2,
- 1b Kuwabe, S. I.; Torraca, K. E.; Buchwald, S. L.. J. Am. Chem. Soc., 2001, 123, 12202.
- 2 Nelson, W. L.; Powell, M. L.. J. Med. Chem., 1979, 22, 1125.
- 3 Campbell, S. F.; Davey, M. J.; Hardstone, J. D.; Lewis, B. N.; Palmer, M. J.. J. Med. Chem., 1987, 30, 49.
- 4 Fang, Q. K.; Grover, P.; Han, Z.; Mcconville, F. X.; Rossi, R. F.; Olsson, D. J.; Kessler, D. W.; Wald, S. A.; Senanayake, C. H.. Tetrahedron: Asymmetry, 2001, 12, 2169.
- 5 Torisu, K.; Kobayashi, K.; Iwahashi, M.; Nakai, Y.; Onoda, T.; Nagase, T.; Sugimoto, I.; Okada, Y.; Matsumoto, R.; Nanbu, F.; Ohuchida, S.; Nakai, H.; Toda, M.. Bioorg. Med. Chem., 2004, 12, 5361.
- 6 Bolognesi, M.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tummiatti, V.; Melchiorre, C.. J. Med. Chem., 1999, 42, 4214.
- 7 Bolchi, C.; Fumagalli, L.; Moroni, B.; Pallavicini, M.; Valoti, E.. Tetrahedron: Asymmetry, 2003, 14, 3779 and the references cited therein.
- 8 Kobayashi, M.; Shimizu, S.. FEMS Microbiol. Lett., 1994, 120, 217 and references cited therein.
- 9a Meth-Cohn, O.; Wang, M. X.. J. Chem. Soc., Perkin Trans. 1, 1997, 1099.
- 9b Meth-Cohn, O.; Wang, M. X.. J. Chem. Soc., Perkin Trans. 1, 1997, 3197 and references cited therein.
- 10 Nagasawa, T.; Schimizu, H.; Yamada, H.. Appl. Microbiol. Biotechnol., 1993, 40, 189.
- 11For recent reviews, see:
- 11a Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H.. Biosci. Biotechnol., Biochem., 1997, 61, 1419.
- 11b Wang, M. X.. Top. Catal., 2005, 35, 117.
- 12Rhodococcus erythropolisAJ270, formerly called, Rhodococcussp. AJ270, is a nitrile hydratase/amidase containing microbial strain.
- 12a Blakey, A. J.; Colby, J.; Williams, E.; O'Reilly, C.. FEMS Microbiol. Lett., 1995, 129, 57.
- 12b O'Mahony, R.; Doran, J.; Coffey, L.; Cahill, O. J.; Black, G. W.; O'Reilly, C.. Antonie van Leeuwenhoek, 2005, 87, 221.
- 13For examples of, Rhodococcus erythropolisAJ270-catalyzed enantioselective biotransformations, see:
- 13a Wang, M. X.; Deng, G.; Wang, D. X.; Zheng, Q.-Y.. J. Org. Chem., 2005, 70, 2439.
- 13b Wang, M. X.; Liu, J.; Wang, D. X.; Zheng, Q. Y.. Tetrahedron: Asymmetry, 2005, 16, 2409.
- 13c Wang, M. X.; Lin, S. J.; Liu, J.; Zheng, Q. Y.. Adv. Synth. Catal., 2004, 346, 439.
- 13d Wang, M. X.; Feng, G. Q.; Zheng, Q. Y.. Tetrahedron: Asymmetry, 2004, 15, 347.
- 13e Wang, M. X.; Feng, G. Q.; Zheng, Q. Y.. Adv. Synth. Catal., 2003, 345, 695.
- 13f Wang, M. X.; Lin, S. J.; Liu, C. S.; Zheng, Q. Y.; Li, J. S.. J. Org. Chem., 2003, 68, 4570.
- 13g Wang, M. X.; Lin, S. J.. J. Org. Chem., 2002, 67, 6542.
- 13h Wang, M. X.; Zhao, S. M.. Tetrahedron Lett., 2002, 43, 6617.
- 13i Wang, M. X.; Zhao, S. M.. Tetrahedron: Asymmetry, 2002, 13, 1695.
- 13j Wang, M. X.; Feng, G. Q.. New J. Chem., 2002, 1575.
- 13k Wang, M. X.; Feng, G. Q.. J. Mol. Catal. B: Enzym., 2002, 18, 267.
- 13l Wang, M. X.; Li, J. J.; Ji, G. J.; Li, J. S.. J. Mol. Catal. B: Enzym., 2001, 14, 77.
- 13m Wang, M. X.; Lin, S. J.. Tetrahedron Lett., 2001, 42, 6925.
- 13n Wang, M. X.; Liu, C. S.; Li, J. S.. Tetrahedron: Asymmetry, 2001, 12, 3367.
- 13o Wang, M. X.; Liu, C. S.; Li, J. S.; Meth-Cohn, O.. Tetrahedron Lett., 2000, 41, 8549.
- 13p Wang, M. X.; Feng, G. Q.. Tetrahedron Lett., 2000, 41, 6501.
- 13q Wang, M. X.; Lu, G.; Ji, G. J.; Huang, Z. T.; Meth-Cohn, O.; Colby, J.. Tetrahedron: Asymmetry, 2000, 11, 1123.
- 13r Feng, G. Q.; Wang, M. X.. Chin. J. Chem., 2001, 19, 1.
- 13s Zhao, S. M.; Wang, M. X.. Chin. J. Chem., 2002, 20, 1291.
- 14 Tomiyama, T.; Wakabayashi, S.; Yokata, M.. J. Med. Chem., 1989, 32, 1988.
- 15a Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J.. J. Am. Chem. Soc., 1982, 104, 7294.
- 15b Program "Selectivity" by Faber, K.; Hoenig, H. http:// www. cis. TUGraz. at/orgc/.
- 16 Racemic amides were prepared from the chemical hydrolysis of nitrile according to the reference: Kamal, A.; Khanna, G. B.; Ramu, R.. Tetrahedron: Asymmetry, 2002, 13, 2039.
- 17 Koo, J.; Avakian, S.; Martin, G. J.. J. Am. Chem. Soc., 1955, 77, 5373.
