Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides: Stereoselectivity and use for kinetic resolution and asymmetrization

Tetrahedron Asymmetry

Volumn 9, Issue 7, 1998, Pages 1097-1102

  Matoishi, Kaori ^a   Sano, Akio ^a   Imai, Nori ^a   Yamazaki, Takahiro ^a   Yokoyama, Masahiro ^a   Sugai, Takeshi ^a   Ohta, Hiromichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 BENZOYLOXY 3 CYCLOHEXENE 1 CARBOXAMIDE; AMIDASE; AMIDE; METHYL 5 HYDROXY 3 CYCLOHEXENE 1 CARBOXYLATE; NITRILE; NITRILE HYDRATASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; ENANTIOMER; HYDROLYSIS; KINETICS; ORGANIC CHEMISTRY; PRIORITY JOURNAL; RHODOCOCCUS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032499238     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00084-6     Document Type: Article

References (30)

1. Review: Crosby, J.; Moilliet, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans 1 1994, 1679-1687. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotech. Biochem. 1997, 61, 1419-1427. Recent examples: Hayashi, T.; Yamamoto, K.; Matsuo, A.; Otsubo, K.; Muramatsu, S.; Matsuda, A.; Komatsu, K. J. Ferment. Bioeng. 1997, 83, 139-145. Eichhorn, E.; Roduit, J.-P.; Shaw, N.; Heinzmann, K.; Kiener, A. Tetrahedron: Asymmetry 1997, 8, 2533-2536. Meth-Cohn, O.; Wang, M.-X. Chem. Commun. 1997, 1041-1042.
2. Review: Crosby, J.; Moilliet, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans 1 1994, 1679-1687. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotech. Biochem. 1997, 61, 1419-1427. Recent examples: Hayashi, T.; Yamamoto, K.; Matsuo, A.; Otsubo, K.; Muramatsu, S.; Matsuda, A.; Komatsu, K. J. Ferment. Bioeng. 1997, 83, 139-145. Eichhorn, E.; Roduit, J.-P.; Shaw, N.; Heinzmann, K.; Kiener, A. Tetrahedron: Asymmetry 1997, 8, 2533-2536. Meth-Cohn, O.; Wang, M.-X. Chem. Commun. 1997, 1041-1042.
3. Review: Crosby, J.; Moilliet, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans 1 1994, 1679-1687. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotech. Biochem. 1997, 61, 1419-1427. Recent examples: Hayashi, T.; Yamamoto, K.; Matsuo, A.; Otsubo, K.; Muramatsu, S.; Matsuda, A.; Komatsu, K. J. Ferment. Bioeng. 1997, 83, 139-145. Eichhorn, E.; Roduit, J.-P.; Shaw, N.; Heinzmann, K.; Kiener, A. Tetrahedron: Asymmetry 1997, 8, 2533-2536. Meth-Cohn, O.; Wang, M.-X. Chem. Commun. 1997, 1041-1042.
4. Review: Crosby, J.; Moilliet, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans 1 1994, 1679-1687. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotech. Biochem. 1997, 61, 1419-1427. Recent examples: Hayashi, T.; Yamamoto, K.; Matsuo, A.; Otsubo, K.; Muramatsu, S.; Matsuda, A.; Komatsu, K. J. Ferment. Bioeng. 1997, 83, 139-145. Eichhorn, E.; Roduit, J.-P.; Shaw, N.; Heinzmann, K.; Kiener, A. Tetrahedron: Asymmetry 1997, 8, 2533-2536. Meth-Cohn, O.; Wang, M.-X. Chem. Commun. 1997, 1041-1042.
5. Review: Crosby, J.; Moilliet, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans 1 1994, 1679-1687. Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotech. Biochem. 1997, 61, 1419-1427. Recent examples: Hayashi, T.; Yamamoto, K.; Matsuo, A.; Otsubo, K.; Muramatsu, S.; Matsuda, A.; Komatsu, K. J. Ferment. Bioeng. 1997, 83, 139-145. Eichhorn, E.; Roduit, J.-P.; Shaw, N.; Heinzmann, K.; Kiener, A. Tetrahedron: Asymmetry 1997, 8, 2533-2536. Meth-Cohn, O.; Wang, M.-X. Chem. Commun. 1997, 1041-1042.
6. Nishise, H.; Kurihara, M.; Tani, Y. Agric. Biol. Chem. 1987, 51, 2613-2616. Tani, Y; Kurihara, M.; Nishise, H.; Yamamoto, K. Agric. Biol. Chem. 1989, 53, 3143-3149. Yamamoto, K.; Ueno, Y.; Otsubo, K.; Yamane, H.; Komatsu, K.; Tani, Y. J. Ferment Bioeng. 1992, 73, 125-129. Robins, K.; Gilligan, T. Eur. Pat. Appl. EP 502,525 (CA. 118: 37548r); Zimmermann, T.; Robins, K.; Birch, O. M.; Boehlen, E. Eur. Pat. Appl. EP 524,604 (CA. 118: 211426m).
7. Nishise, H.; Kurihara, M.; Tani, Y. Agric. Biol. Chem. 1987, 51, 2613-2616. Tani, Y; Kurihara, M.; Nishise, H.; Yamamoto, K. Agric. Biol. Chem. 1989, 53, 3143-3149. Yamamoto, K.; Ueno, Y.; Otsubo, K.; Yamane, H.; Komatsu, K.; Tani, Y. J. Ferment Bioeng. 1992, 73, 125-129. Robins, K.; Gilligan, T. Eur. Pat. Appl. EP 502,525 (CA. 118: 37548r); Zimmermann, T.; Robins, K.; Birch, O. M.; Boehlen, E. Eur. Pat. Appl. EP 524,604 (CA. 118: 211426m).
8. Nishise, H.; Kurihara, M.; Tani, Y. Agric. Biol. Chem. 1987, 51, 2613-2616. Tani, Y; Kurihara, M.; Nishise, H.; Yamamoto, K. Agric. Biol. Chem. 1989, 53, 3143-3149. Yamamoto, K.; Ueno, Y.; Otsubo, K.; Yamane, H.; Komatsu, K.; Tani, Y. J. Ferment Bioeng. 1992, 73, 125-129. Robins, K.; Gilligan, T. Eur. Pat. Appl. EP 502,525 (CA. 118: 37548r); Zimmermann, T.; Robins, K.; Birch, O. M.; Boehlen, E. Eur. Pat. Appl. EP 524,604 (CA. 118: 211426m).
9. Nishise, H.; Kurihara, M.; Tani, Y. Agric. Biol. Chem. 1987, 51, 2613-2616. Tani, Y; Kurihara, M.; Nishise, H.; Yamamoto, K. Agric. Biol. Chem. 1989, 53, 3143-3149. Yamamoto, K.; Ueno, Y.; Otsubo, K.; Yamane, H.; Komatsu, K.; Tani, Y. J. Ferment Bioeng. 1992, 73, 125-129. Robins, K.; Gilligan, T. Eur. Pat. Appl. EP 502,525 (CA. 118: 37548r); Zimmermann, T.; Robins, K.; Birch, O. M.; Boehlen, E. Eur. Pat. Appl. EP 524,604 (CA. 118: 211426m).
10. Nishise, H.; Kurihara, M.; Tani, Y. Agric. Biol. Chem. 1987, 51, 2613-2616. Tani, Y; Kurihara, M.; Nishise, H.; Yamamoto, K. Agric. Biol. Chem. 1989, 53, 3143-3149. Yamamoto, K.; Ueno, Y.; Otsubo, K.; Yamane, H.; Komatsu, K.; Tani, Y. J. Ferment Bioeng. 1992, 73, 125-129. Robins, K.; Gilligan, T. Eur. Pat. Appl. EP 502,525 (CA. 118: 37548r); Zimmermann, T.; Robins, K.; Birch, O. M.; Boehlen, E. Eur. Pat. Appl. EP 524,604 (CA. 118: 211426m).
11. Sugai, T.; Yokoyama, M.; Yamazaki, T.; Ohta, H. Chem. Lett. 1997, 797-798.
12. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299. In the case of meso-substrates, the e.e. of the products is considered to reflect the relative reaction rate between enantiotopic groups.
13. R (min): 74.4 (1S,6R), 81.0 (1R,6S). The absolute configuration was confirmed by preparing an authentic sample from a known half ester (1R,6S)-36: see Kobayashi, S.; Kamiyama, K.; Iimori, T; Ohno, M. Tetrahedron Lett. 1984, 25, 2557-2560.
14. R (min): 15.3 (1S,2R), 17.4 (1R,2S). The absolute configuration was related to that in entries 10-14 by hydrogenation of the product (Fig. 2).
15. R (min): 15.3 (1S,2R), 17.4 (1R,2S). The absolute configuration was related to that in entries 10-14 by hydrogenation of the product (Fig. 2).
16. R (min): 15.3 (1S,2R), 17.4 (1R,2S). The absolute configuration was related to that in entries 10-14 by hydrogenation of the product (Fig. 2).
17. R (min): 25.8 (1R,5R), 31.7 (1S,5S). The absolute configurations of 33 and 34 were determined at the stage of 35, respectively.
18. The hydrolysis had worked well with the substrates bearing benzoyloxy groups: Kakeya, H.; Sakai, N.; Sano, A.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823-1824.; Yokoyama, M.; Imai, N.; Sugai, T; Ohta, H. J. Mol. Catal. Sect. B enzymatic 1996, 1, 135-141. In a certain case, however, the hydrolysis became very slow by introducing a too bulky protecting group such as TBDMS: Sugai, T.; Katoh, O.; Ohta, H. Tetrahedron 1995, 51, 11987-11988.
19. The hydrolysis had worked well with the substrates bearing benzoyloxy groups: Kakeya, H.; Sakai, N.; Sano, A.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823-1824.; Yokoyama, M.; Imai, N.; Sugai, T; Ohta, H. J. Mol. Catal. Sect. B enzymatic 1996, 1, 135-141. In a certain case, however, the hydrolysis became very slow by introducing a too bulky protecting group such as TBDMS: Sugai, T.; Katoh, O.; Ohta, H. Tetrahedron 1995, 51, 11987-11988.
20. The hydrolysis had worked well with the substrates bearing benzoyloxy groups: Kakeya, H.; Sakai, N.; Sano, A.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823-1824.; Yokoyama, M.; Imai, N.; Sugai, T; Ohta, H. J. Mol. Catal. Sect. B enzymatic 1996, 1, 135-141. In a certain case, however, the hydrolysis became very slow by introducing a too bulky protecting group such as TBDMS: Sugai, T.; Katoh, O.; Ohta, H. Tetrahedron 1995, 51, 11987-11988.
21. The preference of same enantiomer and/or enantiotopic group by nitrile hydratase and amidase was observed in entry 2, 7 and 9. Related example: Beard, T.; Cohen, M. A.; Parratt, J. S.; Turner, N. J.; Crosby, J.; Moilliet, J. Tetrahedron: Asymmetry 1993, 4, 1085-1104.
22. Deigner, H. P.; Blencowe, C.; Freyberg, C. E. J. Mol. Catal. B: Enz. 1996, 1, 61-70.
23. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
24. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
25. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
26. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
27. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
28. Smith III A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riéra, A. Tetrahedron Lett. 1989, 30, 6963-6966. Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9-10. Kuwahara, S.; Mori, K. Tetrahedron 1990, 46, 8075-8082. Trost, B. M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613-1616. Enzymatic preparation of related compounds: Gu, R.-L.; Sih, C. J. Tetrahedron Lett. 1990, 31, 3287-3290. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859-1862.
29. Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230-7237.
30. 3); IR and NMR spectra were identical with those of (1R,5R)-35.